ChemicalBook CAS DataBase List PD 0332991 HCl

PD 0332991 HCl synthesis

4synthesis methods

Product Name:PD 0332991 HCl
CAS Number:827022-32-2
Molecular formula:C24H30ClN7O2
Molecular Weight:484

4-{6-[8-CYCLOPENTYL-6-(1-ETHOXY-VINYL)-5-METHYL-7-OXO-7,8-DIHYDRO-PYRIDO[2,3-D]PYRIMIDIN-2-YLAMINO]-PYRIDIN-3-YL}-PIPERAZINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER

571189-10-1

827022-32-2

Synthesis of 6-acetyl-8-cyclopentyl-5-methyl-2-((5-(piperazin-1-yl)pyridin-2-yl)amino)pyrido[2,3-d]pyrimidin-7(8H)-one hydrochloride from tert-butyl 4-[6-[[8-cyclopentyl-6-(1-ethoxyethenyl)-5-methyl-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-2-yl]amino]pyridin-3-yl]piperazin-1-carboxylate. [2,3-d]pyrimidin-7(8H)-one hydrochloride was prepared in the following general procedure: to tert-butyl 4-[6-[[8-cyclopentyl-6-(1-ethoxyvinyl)-5-methyl-7-oxo-7,8-dihydropyrido[2,3-D]pyrimidin-2-yl]amino]pyridin-3-yl]piperazine-1-carboxylate under ice-bath cooling conditions (4.50 g. 0.00783 mol, as prepared in Example 2) in a solution of dichloromethane (100 mL) was bubbled with hydrogen chloride gas. The resulting suspension was sealed and stirred overnight at room temperature and subsequently diluted with ether (200 mL). The solid was collected by filtration, washed with ether and dried to afford 6-acetyl-8-cyclopentyl-5-methyl-2-((5-(piperazin-1-yl)pyridin-2-yl)amino)pyrido[2,3-d]pyrimidin-7(8H)-one hydrochloride as a yellow solid (4.01 g, 92% yield).

571189-10-1
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827022-32-2
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Yield:827022-32-2 92%

Reaction Conditions:

with hydrogenchloride in dichloromethane at 0 - 20;

Steps:

3

EXAMPLE 3 Preparation of 6-ACETVL-8-CVCLOPENTVI-5-METHYL-2- (5-PIPERAZIN-1- EL-PVRIDIN-2-YLAMINO)- 8H-PVRIDOR2, 3-DLPYRIMIDIN-7-ONE HVDROCHLORIDE Hydrogen chloride gas was bubbled into an ice-bath cooled solution of 4- {6- [8- CYCLOPENTYL-6- (1-ETHOXY-VINYL)-5-METHYL-7-OXO-7, 8-dihydro-pyrido [2, 3-D] idin-2-ylamino]- PYRIDIN-3-YL}-PIPERAZINE-1-CARBOXYLIC acid tert-butyl ester (4.50 g, 0.00783 mol, prepared as in Example 2) in DCM (100 mL). The resulting suspension was stoppered and stirred at RT overnight, then diluted with diethyl ether (200 mL). The solid was collected by filtration, washed with diethyl ether, and dried to give the hydrochloride salt of 6-acetyl-8-cyclopentyl-5- METHYL-2- (5-PIPERAZIN-1-YL-PYRIDIN-2-YLAMINO)-8H-PYRIDO [2, 3-d] pyrimidin-7-one as a yellow solid (4. 01 g, 92 %).

References:

WO2005/5426,2005,A1 Location in patent:Page/Page column 22