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2-allyl-6-(Methylthio)-1H-pyrazolo[3,4-d]pyriMidin-3(2H)-one

Product Name
2-allyl-6-(Methylthio)-1H-pyrazolo[3,4-d]pyriMidin-3(2H)-one
CAS No.
955368-90-8
Chemical Name
2-allyl-6-(Methylthio)-1H-pyrazolo[3,4-d]pyriMidin-3(2H)-one
Synonyms
2-allyl-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one;EOS-61125;MK-1775 intermediate;MK-1755 intermediate 3;2-allyl-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidin-3-one;2-allyl-6-(Methylthio)-1H-pyrazolo[3,4-d]pyriMidin-3(2H)-one;2-allyl-6-(methylthio)-1,2-dihydropyrazolo[3,4-d]pyrimidin-3-one;6-methylsulfanyl-2-prop-2-enyl-1h-pyrazolo[3,4-d]pyrimidin-3-one;2-allyl-6-(methylthio)-2,5-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one;6-(methylsulfanyl)-2-(prop-2-en-1-yl)-1H,2H,3H-pyrazolo[3,4-d]pyrimidin-3-one
CBNumber
CB82560973
Molecular Formula
C9H10N4OS
Formula Weight
222.27
MOL File
955368-90-8.mol
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2-allyl-6-(Methylthio)-1H-pyrazolo[3,4-d]pyriMidin-3(2H)-one Property

Boiling point:
397.9±44.0 °C(Predicted)
Density 
1.39±0.1 g/cm3(Predicted)
storage temp. 
2-8°C
form 
solid
pka
3.48±0.20(Predicted)
Appearance
Light yellow to yellow Solid
InChI
InChI=1S/C9H10N4OS/c1-3-4-13-8(14)6-5-10-9(15-2)11-7(6)12-13/h3,5H,1,4H2,2H3,(H,10,11,12)
InChIKey
JKBQCALHIQOSTC-UHFFFAOYSA-N
SMILES
C1(SC)=NC=C2C(=O)N(CC=C)NC2=N1
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

TRC
Product number
A621525
Product name
2-Allyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one
Packaging
10mg
Price
$45
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
CHM0387957
Product name
2-ALLYL-6-(METHYLTHIO)-1H-PYRAZOLO[3,4-D]PYRIMIDIN-3(2H)-ONE
Purity
95.00%
Packaging
5MG
Price
$500.83
Updated
2021/12/16
AK Scientific
Product number
6462AC
Product name
2-Allyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one
Packaging
1g
Price
$724
Updated
2021/12/16
Matrix Scientific
Product number
120801
Product name
2-Allyl-6-(methylthio)-1H-pyrazolo-[3,4-d]pyrimidin-3(2H)-one
Purity
97%
Packaging
1g
Price
$1162
Updated
2021/12/16
Matrix Scientific
Product number
120801
Product name
2-Allyl-6-(methylthio)-1H-pyrazolo-[3,4-d]pyrimidin-3(2H)-one
Purity
97%
Packaging
5g
Price
$3592
Updated
2021/12/16
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2-allyl-6-(Methylthio)-1H-pyrazolo[3,4-d]pyriMidin-3(2H)-one Chemical Properties,Usage,Production

Synthesis

5909-24-0

21075-86-5

955368-90-8

The general procedure for the synthesis of 2-allyl-6-(methylmercapto)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one from ethyl 4-chloro-2-methylthio-pyrimidine-5-carboxylate and tert-butyl 1-allylhydrazinecarboxylate was as follows: to a THF solution (150 ml) of ethyl 4-chloro-2-methylthio-5-pyrimidinecarboxylate (11.1 g, 47.8 mmol) DIPEA (20.8 ml, 120 mmol) and tert-butyl 1-allylhydrazinecarboxylate (8.23 g, 47.8 mmol) were added. The reaction mixture was heated to reflux for 72 hours followed by vacuum concentration. Ether (50 ml) was added to the residue and the precipitate was collected by filtration. The filtrate was evaporated to dryness and the residue was cooled in an ice bath before adding trifluoroacetic acid (40 ml). The resulting solution was stirred at room temperature for 1 hour and then continued at 70°C for 1 hour. After the solvent was removed by vacuum, the residue was dissolved in ethanol (50 ml), cooled in an ice bath and 6M sodium hydroxide solution (75 ml) was added. After stirring for 15 minutes at room temperature, it was acidified by adding concentrated hydrochloric acid (40 ml). The orange solution was evaporated to dryness and the residue was partitioned between chloroform (100 ml) and water (100 ml). The organic phase was washed with brine (50 ml), dried over magnesium sulfate and concentrated under vacuum and ground with hexane. The solid precipitate was washed with ethanol and ether and dried under vacuum to give 2-allyl-6-(methylmercapto)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one as a yellow solid (5.44 g, 24.5 mmol, 51% yield). Thin-layer chromatography Rf value was 0.45 (dichloromethane:methanol=9:1); melting point was 125-128 °C; IR spectra (cm^-1) 3032, 2979, 2926, 2659, 1656, 1615, 1561, 1154; 1H NMR (400 MHz, DMSO-d6) δ 2.53 (3H, s, -SCH3), and 4.38 (2H, d, J=5.2 Hz, N2-CH2), 5.06-5.20 (2H, m, allyl C-H cis/trans), 5.87 (1H, ddt, J=17.2, 10.5, 5.3 Hz, olefin CH), 8.67 (1H, s, H-4), 12.65 (1H, s, NH); mass spectrum [M+H ]+ m/z 223.1.

References

[1] Patent: WO2017/75629, 2017, A2. Location in patent: Page/Page column 33; 34
[2] ChemMedChem, 2018, vol. 13, # 16, p. 1681 - 1694
[3] Patent: US2007/254892, 2007, A1. Location in patent: Page/Page column 30-31
[4] Patent: WO2008/133866, 2008, A1. Location in patent: Page/Page column 28
[5] ACS Chemical Biology, 2016, vol. 11, # 4, p. 921 - 930

2-allyl-6-(Methylthio)-1H-pyrazolo[3,4-d]pyriMidin-3(2H)-one Preparation Products And Raw materials

Raw materials

Preparation Products

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2-allyl-6-(Methylthio)-1H-pyrazolo[3,4-d]pyriMidin-3(2H)-one Suppliers

China 72 India 1 United States 7 Global 80
Anhui Shuoyuan Pharmaceutical Technology R&D Co.,Ltd
Tel
05558228005 18151793555
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413315120@qq.com
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China
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Jinan Xinzheng Pharmaceutical Technology Co., Ltd.
Tel
0531-88798968 18615218958
Email
yin3684895@126.com
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China
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182
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58
Shanghai Renshi Pharmatech Co., LTD
Tel
021-61150625 17721318029
Fax
021-26018649
Email
info@renshipharma.com
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China
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161
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Hangzhou Chemtrue Bio-Tech Co.,Ltd.
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0571-86828652 18857119830
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0571-83522824
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sales@chemtrue-bio.com
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China
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252
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PharmaBlock Sciences (Nanjing),Inc.
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025-86918202 4000255188
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86-025-86918232
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sales@pharmablock.com
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China
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5000
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Shanghai ZaiQi Bio-Tech Co., Ltd.
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+86-021-54824098 15317552526
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021-54824069
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sales@chemzq.com
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China
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Tianjin YongSheng Biotechnology Co., Ltd.
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022-60987737 13512258274
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86-022-23500597
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sales@immortalbio.com
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China
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NCE Biomedical Co.,Ltd.
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4000-027-021 |24 +86-13986109188 | +86-15623472865 | +81-08033611988
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+86-27-87599188
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China
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1493
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Shanghai T&W Pharmaceutical Co., Ltd.
Tel
+86 21 61551611
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+86 21 50676805
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China
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9891
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Haoyuan Chemexpress Co., Ltd.
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021-58950125
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(86) 21-58955996
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info@chemexpress.com
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China
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7552
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View Lastest Price from 2-allyl-6-(Methylthio)-1H-pyrazolo[3,4-d]pyriMidin-3(2H)-one manufacturers

Shaanxi Dideu New Materials Co. Ltd
Product
MK-1755 intermediate 3 955368-90-8
Price
US $0.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
1000kg
Release date
2025-09-29
Henan Aochuang Chemical Co.,Ltd.
Product
2-allyl-6-(Methylthio)-1H-pyrazolo[3,4-d]pyriMidin-3(2H)-one 955368-90-8
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
1Ton
Release date
2022-09-22
Career Henan Chemical Co
Product
2-allyl-6-(Methylthio)-1H-pyrazolo[3,4-d]pyriMidin-3(2H)-one 955368-90-8
Price
US $1.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
1kg-1000kg
Release date
2020-01-02

955368-90-8, 2-allyl-6-(Methylthio)-1H-pyrazolo[3,4-d]pyriMidin-3(2H)-oneRelated Search:


  • 2-allyl-6-(Methylthio)-1H-pyrazolo[3,4-d]pyriMidin-3(2H)-one
  • 2-allyl-6-(methylthio)-1,2-dihydropyrazolo[3,4-d]pyrimidin-3-one
  • 2-allyl-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one
  • EOS-61125
  • 1,2-dihydro-6-(Methylthio)-2-(2-propen-1-yl)-3H-Pyrazolo[3,4-d]pyriMidin-3-one
  • 6-methylsulfanyl-2-prop-2-enyl-1h-pyrazolo[3,4-d]pyrimidin-3-one
  • 6-(methylsulfanyl)-2-(prop-2-en-1-yl)-1H,2H,3H-pyrazolo[3,4-d]pyrimidin-3-one
  • MK-1775 intermediate
  • 3H-Pyrazolo[3,4-d]pyrimidin-3-one, 1,2-dihydro-6-(methylthio)-2-(2-propen-1-yl)-
  • 2-allyl-6-(methylthio)-2,5-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one
  • MK-1755 intermediate 3
  • 2-allyl-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidin-3-one
  • 955368-90-8