2-chloro-8-cyclopentyl-5-Methylpyrido[2,3-d]pyriMidin-7(8H)-one

Product Name: 2-chloro-8-cyclopentyl-5-Methylpyrido[2,3-d]pyriMidin-7(8H)-one
CAS No.: 1013916-37-4
Chemical Name: 2-chloro-8-cyclopentyl-5-Methylpyrido[2,3-d]pyriMidin-7(8H)-one
Synonyms: Palbociclib intermediates;-5-methyL;oro-8-cycL;3-d]pyriMidin-7(8H)-one;Palbociclib Impurity 105;Palbociclib Intermediate2;2-chloro-8-cyclopentyl-5-Me;Palbociclib impurity 703-201;pyrido[2,3-d]pyrimidin-7(8H)-one;2-chloro-8-cyclopentyl-5-Methylpyrido[2
CBNumber: CB62554161
Molecular Formula: C13H14ClN3O
Formula Weight: 263.72
MOL File: 1013916-37-4.mol

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2-chloro-8-cyclopentyl-5-Methylpyrido[2,3-d]pyriMidin-7(8H)-one Property

Melting point:: 176 - 178°C
Boiling point:: 428.0±34.0 °C(Predicted)
Density: 1.346±0.06 g/cm3(Predicted)
storage temp.: under inert gas (nitrogen or Argon) at 2-8°C
solubility: Chloroform (Slightly), Methanol (Slightly)
form: Solid
pka: 0.82±0.20(Predicted)
color: Yellow to Dark Yellow
Water Solubility: Slightly soluble in water.
InChI: InChI=1S/C13H14ClN3O/c1-8-6-11(18)17(9-4-2-3-5-9)12-10(8)7-15-13(14)16-12/h6-7,9H,2-5H2,1H3
InChIKey: BSKNQSYIDZUXQT-UHFFFAOYSA-N
SMILES: C1(Cl)=NC=C2C(C)=CC(=O)N(C3CCCC3)C2=N1

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

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

P405Store locked up.

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N-Bromosuccinimide Price

TRC

Product number: C585608
Product name: 2-Chloro-8-cyclopentyl-5-methyl-8H-pyrido[2,3-d]pyrimidin-7-one
Packaging: 1g
Price: $90
Updated: 2021/12/16

Matrix Scientific

Product number: 131623
Product name: 2-Chloro-8-cyclopentyl-5-methylpyrido-[2,3-d]pyrimidin-7(8H)-one
Purity: 97%
Packaging: 25g
Price: $147
Updated: 2021/12/16

AK Scientific

Product number: J20498
Product name: 2-Chloro-8-cyclopentyl-5-methylpyrido[2,3-d]pyrimidin-7(8H)-one
Packaging: 5g
Price: $67
Updated: 2021/12/16

AK Scientific

Product number: 0375AA
Product name: 2-Chloro-8-cyclopentyl-5-methylpyrido[2,3-d]pyrimidin-7(8H)-one
Packaging: 5g
Price: $25
Updated: 2021/12/16

AK Scientific

Product number: J99451
Product name: 2-Chloro-8-cyclopentyl-5-methylpyrido[2,3-d]pyrimidin-7(8H)-one
Packaging: 10g
Price: $28
Updated: 2021/12/16

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2-chloro-8-cyclopentyl-5-Methylpyrido[2,3-d]pyriMidin-7(8H)-one Chemical Properties,Usage,Production

Description

2-chloro-8-cyclopentyl-5-Methylpyrido[2,3-d]pyriMidin-7(8H)-one is used as an intermediate for Palbociclib, a CDK 4/6 inhibitor used to treat patients with hormone receptor (HR)-positive, HER-2-negative advanced or metastatic (cancer that has spread) breast cancer.

Uses

2-Chloro-8-cyclopentyl-5-methyl-8H-pyrido[2,3-d]pyrimidin-7-one is used as pharmaceutical intermediate.

Synthesis

733039-20-8

107-93-7

1013916-37-4

To the reaction vessel was added 5-bromo-2-chloro-N-cyclopentyl-4-pyrimidinamine (10.0 g, 1.0 eq.) and N-methylpyrrolidone (NMP, 50 mL, 5.0 vol.) at room temperature. Subsequently, crotonic acid (4.7 g, 1.5 eq.) and triethylamine (20.2 mL, 4.0 eq.) were added to the reaction mixture. The vessel was degassed and purged three times with nitrogen. Palladium acetate (Pd(OAc)2, 0.25 g, 0.03 eq.) was added to the degassed reaction mixture. The vessel was again degassed and purged with nitrogen three times in the same manner. The reaction mixture was heated to 65 °C and stirred continuously until the feedstock was completely consumed (at least 6 hours). Then, acetic anhydride (6.8 mL, 2.0 eq.) was added to the reaction mixture. The reaction was kept at 65 °C until the feedstock was completely consumed (usually takes 1-2 hours). Upon completion of the reaction, the mixture was cooled to 20 °C and water (100 mL, 10 v/v) was added to dissolve the triethylamine-HBr salt while 2-chloro-8-cyclopentyl-5-methyl-8H-pyrido[2,3-d]pyrimidin-7(8H)-one was precipitated. The precipitate was stirred at 20°C for 1 hour. The solid was collected by filtration and washed sequentially with a mixture of water (20 mL, 2.0 v/v) and isopropanol/water (4:1, 50 mL, 5.0 v/v). Finally, the crude product was vacuum dried at 55-70 °C to afford 2-chloro-8-cyclopentyl-5-methyl-8H-pyrido[2,3-d]pyrimidin-7(8H)-one (7.8 g, 81% yield) as a tan to gray solid.

References

[1] Patent: WO2014/128588, 2014, A1. Location in patent: Page/Page column 34; 35
[2] Patent: WO2008/32157, 2008, A2. Location in patent: Page/Page column 26

2-chloro-8-cyclopentyl-5-Methylpyrido[2,3-d]pyriMidin-7(8H)-one Preparation Products And Raw materials

Raw materials

Preparation Products

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2-chloro-8-cyclopentyl-5-Methylpyrido[2,3-d]pyriMidin-7(8H)-one Suppliers

China 267 India 8 United States 7 Global 282

Tianjin Branch Chong pharmaceutical intermediates Co., Ltd.

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View Lastest Price from 2-chloro-8-cyclopentyl-5-Methylpyrido[2,3-d]pyriMidin-7(8H)-one manufacturers

ShenZhen H&D Pharmaceutical Technology Co., LTD

Product: Palbociclib Impurity 9 1013916-37-4
Price: US $0.00-0.00/mg
Min. Order: 10mg
Purity: 98%
Supply Ability: 500mg
Release date: 2024-08-13

Career Henan Chemical Co

Product: 2-chloro-8-cyclopentyl-5-Methylpyrido[2,3-d]pyriMidin-7(8H)-one 1013916-37-4
Price: US $100.00/KG
Min. Order: 1KG
Purity: 98%
Supply Ability: 100KG
Release date: 2018-07-26

1013916-37-4, 2-chloro-8-cyclopentyl-5-Methylpyrido[2,3-d]pyriMidin-7(8H)-oneRelated Search:

4-[6-[(8-cyclopentyl-6-ethenyl-7,8-dihydro-5-methyl-7-oxopyrido[2,3-d]pyrimidin-2-yl)amino]-3-pyridinyl]-1-piperazinecarboxylic acid tert-butyl ester 4-(5-AMINOPYRIDIN-2-YL)PIPERAZINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER tert-Butyl 4-(6-((6-(1-butoxyvinyl)-8-cyclopentyl-5-methyl-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-2-yl)amino)pyridin-3-yl)piperazine-1-carboxylate 2-Amino-5-bromopyridine Palbociclib Impurity 7 4-[6-(6-BROMO-8-CYCLOPENTYL-5-METHYL-7-OXO-7,8-DIHYDRO-PYRIDO[2,3-D]PYRIMIDIN-2-YLAMINO)-PYRIDIN-3-YL]-PIPERAZINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER Pyrido[2,3-d]pyriMidin-7(8H)-one, 8-cyclopentyl-5-Methyl-2-[[5-(1-piperazinyl)-2-pyridinyl]aMino]- Phosphine oxide, tris (2-methylphenyl)- tert-butyl 4-(6-((6-acetyl-8-cyclopentyl-5-methyl-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-2-yl)amino)pyridin-3-yl)piperazine-1-carboxylate 1-Piperazinecarboxylic acid, 4-(2-aMino-3-pyridinyl)-, 1,1-diMethylethyl ester 5-(piperazin-1-yl)pyridin-2-aMine 571188-59-5 8-cyclopentyl-6-(1-hydroxyethyl)-5-methyl-2-((5-(piperazin-1-yl)pyridin-2-yl)amino)pyrido[2,3-d]pyrimidin-7(8H)-one 1,4-bis(4-nitrophenyl)piperazine 1-(5-Nitropyridin-2-yl)piperazine 6-broMo-8-cyclopentyl-5-Methyl-2-(5-(piperazin-1-yl)pyridin-2-ylaMino)pyrido[2,3-d]pyriMidin-7(8H)-one

2-chloro-8-cyclopentyl-5-Methylpyrido[2,3-d]pyriMidin-7(8H)-one

Pyrido[2,3-d]pyriMidin-7(8H)-one, 2-chloro-8-cyclopentyl-5-Methyl-

2-chloro-8-cyclopentyl-5-Me

Palbociclib Intermediate2

Palbociclib intermediates

2-Chloro-8-cyclopentyl-5-methyl-8H-pyrido[2,3-d]pyrimidin-7-one (For Palbociclib)

2-chloro-8-cyclopentyl-5-methylpyrido[2,3-d]pyrimidin-7-one

2-chloro-8-cyclopentyl-5-methyl-7H,8H-pyrido[2,3-d]pyrimidin-7-one

2-chloro-8-cyclopentyl-5-Methylpyrido[2

3-d]pyriMidin-7(8H)-one

2-Chloro-8-cyclopentyl-5-methyl-8H-pyrido[2,3-d]pyrimidin-7-one

oro-8-cycL

pyrido[2,3-d]pyrimidin-7(8H)-one

2-Chloro-8-cyclopentyl-5-methyl-8H-pyrido[2,3-d]pyrimidin-7-one,97%

-5-methyL

2-chloro-8-cyclopentyl-5-Methylpyrido[2,3-d]pyriMidin-7(8H)-one 2-

2-chloro-8-cyclopentyl-5-methylpyrido[2,3-d]pyrimidin-7(8H)-...

Palbociclib Impurity 105

2-chloro-8-cyclopentyl-5-methylpyrido[2,3-d]

2-chloro-8-cyclopentyl-5-Methylpyrido[2,3-d]pyriMi

2-chloro-8-cyclopentyl-5-methoyrido-8H-pyrido[ 2,3-D]pyrimidin- 7 - one

2-Chloro-8-cyclopentyl-5-methyl-8H-pyrido[2,3-

2-chloro-8-cyclopentyl-5-methyl-8H-pyrido [2,3-D] pyridine

Palbociclib impurity 703-201

1013916-37-4

Anticancer

1013916-37-4