ChemicalBook > CAS DataBase List > (4-AMINO-2-(METHYLTHIO)PYRIMIDIN-5-YL)METHANOL

(4-AMINO-2-(METHYLTHIO)PYRIMIDIN-5-YL)METHANOL

Product Name
(4-AMINO-2-(METHYLTHIO)PYRIMIDIN-5-YL)METHANOL
CAS No.
588-36-3
Chemical Name
(4-AMINO-2-(METHYLTHIO)PYRIMIDIN-5-YL)METHANOL
Synonyms
Methioprim;(4-AMINO-2-(METHYLTHIO)PYRIMIDIN-5-YL)ME...;4-AMINO-2-(METHYLTHIO)-5-PYRIMIDINEMETHANOL;4-Amino-2-(methylthio)-5-pyrimidinyl]methanol;5-Pyrimidinemethanol, 4-amino-2-(methylthio)-;4-AMINO-2-METHYLMERCAPTO-PYRIMIDINE-4-CARBINOL;(4-AMINO-2-(METHYLTHIO)PYRIMIDIN-5-YL)METHANOL;4-AMINO-5-HYDROXYMETHYL-2-(METHYLTHIO)PYRIMIDINE;(4-AMINO-2-METHYLSULFANYL-PYRIMIDIN-5-YL)-METHANOL;(4-azanyl-2-methylsulfanyl-pyrimidin-5-yl)methanol
CBNumber
CB3387753
Molecular Formula
C6H9N3OS
Formula Weight
171.22
MOL File
588-36-3.mol
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(4-AMINO-2-(METHYLTHIO)PYRIMIDIN-5-YL)METHANOL Property

Melting point:
126-127°
Boiling point:
408.6±30.0 °C(Predicted)
Density 
1.38±0.1 g/cm3(Predicted)
storage temp. 
under inert gas (nitrogen or Argon) at 2–8 °C
solubility 
DMSO (Slightly), Methanol (Slightly)
form 
Solid
pka
13.08±0.10(Predicted)
color 
Off-White to Pale Yellow
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Safety

HS Code 
29335990
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P310Immediately call a POISON CENTER or doctor/physician.

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N-Bromosuccinimide Price

TRC
Product number
M260520
Product name
Methioprim
Packaging
25mg
Price
$315
Updated
2021/12/16
TRC
Product number
M260520
Product name
Methioprim
Packaging
100mg
Price
$1110
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
CHM1051884
Product name
4-AMINO-2-METHYLMERCAPTO-PYRIMIDINE-4-CARBINOL
Purity
95.00%
Packaging
5G
Price
$1888.43
Updated
2021/12/16
SynQuest Laboratories
Product number
8H66-1-6F
Product name
[4-Amino-2-(methylsulfanyl)pyrimidin-5-yl]methanol
Purity
97.0%
Packaging
5G
Price
$790
Updated
2021/12/16
Matrix Scientific
Product number
071115
Product name
(4-Amino-2-(methylthio)pyrimidin-5-yl)methanol
Purity
97%
Packaging
5g
Price
$1035
Updated
2021/12/16
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(4-AMINO-2-(METHYLTHIO)PYRIMIDIN-5-YL)METHANOL Chemical Properties,Usage,Production

Chemical Properties

(4-AMINO-2-(METHYLTHIO)PYRIMIDIN-5-YL)METHANOL is white cryst powder

Uses

(4-AMINO-2-(METHYLTHIO)PYRIMIDIN-5-YL)METHANOL is an intermediate used in the synthesis of Thiamine (T344185). Also, used for the preparation of pyridopyrimidines and naphthyridines as inhibitors of Akt kinase for the treatment of cancer.

Uses

Tumor antagonist in mice.

Synthesis

776-53-4

588-36-3

General procedure for the synthesis of 2-(methylthio)-4-aminopyrimidine-5-carboxylic acid from ethyl 2-(methylthio)-4-aminopyrimidine-5-carboxylate: ethyl 4-amino-2-(methylthio)pyrimidine-5-carboxylate (72.3 g, 339 mmol) was dissolved in tetrahydrofuran (THF, 900 mL) and the solution was cooled to 0 °C. A solution of LiAlH4 (2 M in THF, 195 mL, 390 mmol) was added slowly and dropwise over 1 hour. The reaction mixture was kept stirred at 0 °C for 2 h, then allowed to warm slowly to room temperature and continued stirring overnight. Upon completion of the reaction, the mixture was again cooled to 0 °C and water (15 mL), 20% aqueous potassium hydroxide solution (15 mL) and water (30 mL) were carefully added in turn to quench the reaction. The resulting mixture was stirred for 1 hour. Subsequently, it was dried with anhydrous magnesium sulfate (MgSO4), filtered, and the filtrate was concentrated under reduced pressure and finally dried under vacuum to afford the target product 2-methylthio-4-aminopyrimidine-5-methanol (55.85 g, 96% yield). Mass spectrometry (MS) analysis showed m/z: 172.1 ([M + H]+).

References

[1] Journal of Medicinal Chemistry, 2005, vol. 48, # 7, p. 2371 - 2387
[2] Patent: WO2013/134243, 2013, A1. Location in patent: Page/Page column 16
[3] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4165 - 4179
[4] Patent: WO2014/151682, 2014, A1. Location in patent: Page/Page column 57; 58
[5] Journal of Medicinal Chemistry, 2014, vol. 57, # 3, p. 578 - 599

(4-AMINO-2-(METHYLTHIO)PYRIMIDIN-5-YL)METHANOL Preparation Products And Raw materials

Raw materials

Ethanol Acetic anhydride Triethyl orthoformate Toluene Sodium Tetrahydrofuran Lithium Aluminum Hydride N,N-Dimethylformamide dimethyl acetal Isopropyl alcohol Ethyl cyanoacetate Thiourea

Preparation Products

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View Lastest Price from (4-AMINO-2-(METHYLTHIO)PYRIMIDIN-5-YL)METHANOL manufacturers

Dideu Industries Group Limited
Product
(4-AMINO-2-(METHYLTHIO)PYRIMIDIN-5-YL)METHANOL 588-36-3
Price
US $1.10/g
Min. Order
1g
Purity
99.00%
Supply Ability
100 Tons Min
Release date
2021-12-13
Career Henan Chemical Co
Product
(4-AMINO-2-(METHYLTHIO)PYRIMIDIN-5-YL)METHANOL 588-36-3
Price
US $8.80/KG
Min. Order
1KG
Purity
97%-99%
Supply Ability
100kg
Release date
2019-08-08

588-36-3, (4-AMINO-2-(METHYLTHIO)PYRIMIDIN-5-YL)METHANOLRelated Search:

4-AMINO-2-(ETHYLTHIO)-5-(HYDROXYMETHYL)PYRIMIDINE Ethyl 4-amino-2-(ethylthio)-5-pyrimidinecarboxylate 4-AMINO-5-CARBOXY-2-ETHYL-MERCAPTOPYRIMIDINE ETHYL 4-AMINO-2-(METHYLTHIO)PYRIMIDINE-5-CARBOXYLATE 5-Pyrimidinemethanol ETHYL 4-(BENZYLAMINO)-2-(METHYLTHIO)PYRIMIDINE-5-CARBOXYLATE ETHYL 4-(METHYLAMINO)-2-(METHYLSULFANYL)-5-PYRIMIDINECARBOXYLATE {[4-AMINO-5-(ETHOXYCARBONYL)PYRIMIDIN-2-YL]THIO}ACETIC ACID ETHYL 4-(4-CHLOROANILINO)-2-(METHYLSULFANYL)-5-PYRIMIDINECARBOXYLATE ETHYL 2-(METHYLSULFANYL)-4-MORPHOLINO-5-PYRIMIDINECARBOXYLATE ETHYL 2-(METHYLSULFANYL)-4-PIPERIDINO-5-PYRIMIDINECARBOXYLATE ETHYL 4-(3,4-DICHLOROANILINO)-2-(METHYLSULFANYL)-5-PYRIMIDINECARBOXYLATE ETHYL 4-(DIMETHYLAMINO)-2-(METHYLSULFANYL)-5-PYRIMIDINECARBOXYLATE BUTTPARK 21\09-28 ETHYL 2-(METHYLSULFANYL)-4-[4-(TRIFLUOROMETHYL)ANILINO]-5-PYRIMIDINECARBOXYLATE ETHYL 4-[3,5-BIS(TRIFLUOROMETHYL)ANILINO]-2-(METHYLSULFANYL)-5-PYRIMIDINECARBOXYLATE RARECHEM AL FB 0074 4-AMINO-2-METHYLSULFANYL-PYRIMIDINE-5-CARBOXYLIC ACID

  • 4-AMINO-2-(METHYLTHIO)-5-PYRIMIDINEMETHANOL
  • 4-AMINO-5-HYDROXYMETHYL-2-(METHYLTHIO)PYRIMIDINE
  • Methioprim
  • (4-azanyl-2-methylsulfanyl-pyrimidin-5-yl)methanol
  • (4-AMINO-2-(METHYLTHIO)PYRIMIDIN-5-YL)METHANOL
  • (4-AMINO-2-METHYLSULFANYL-PYRIMIDIN-5-YL)-METHANOL
  • 4-AMINO-2-METHYLMERCAPTO-PYRIMIDINE-4-CARBINOL
  • (4-AMINO-2-(METHYLTHIO)PYRIMIDIN-5-YL)ME...
  • 5-Pyrimidinemethanol, 4-amino-2-(methylthio)-
  • (4-AMINO-2-(METHYLTHIO)PYRIMIDIN-5-YL)METHANOL ISO 9001：2015 REACH
  • 4-Amino-2-(methylthio)-5-pyrimidinyl]methanol
  • 588-36-3
  • Amines
  • Aromatics
  • Heterocycles
  • Sulfur & Selenium Compounds