ChemicalBook > CAS DataBase List > 2-chloro-8-cyclopentyl-5-Methylpyrido[2,3-d]pyriMidin-7(8H)-one
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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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