3-(2-Chloroethyl)-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one Chemical Properties

Melting point:

68.5-69.5 °C

Boiling point:

337 °C

Density 

1.30

Flash point:

157 °C

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

3.58±0.70(Predicted)

color 

White to Off-White

InChI

InChI=1S/C11H15ClN2O/c1-8-9(5-6-12)11(15)14-7-3-2-4-10(14)13-8/h2-7H2,1H3

InChIKey

CMWCQQUYLPYOMY-UHFFFAOYSA-N

SMILES

C12CCCCN1C(=O)C(CCCl)=C(C)N=2

CAS DataBase Reference

63234-80-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

T

Risk Statements 

25

Safety Statements 

45

RIDADR 

UN3261

HS Code 

2933.99.9701

HazardClass 

IRRITANT

3-(2-Chloroethyl)-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one Usage And Synthesis

Chemical Properties

White Solid

Uses

3-(2-Chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one (Risperidone EP Impurity L) is an intermediate in the synthesis of Risperidone (R525000), which is a combined serotonin (5-HT2) and dopamine (D2) receptor antagonist.

Synthesis

The general procedure for the synthesis of 3-(2-chloroethyl)-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one from 3-(2-chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one is as follows: 28 g of 3-(2-chloroethyl)-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one obtained in step A) was dissolved in 90 mL 6N hydrochloric acid. -a]pyrimidin-4-one was dissolved in 90 mL of 6N hydrochloric acid, followed by the addition of 2.8 g of 10% palladium carbon catalyst to the solution. The reaction mixture was subjected to 35 psi hydrogen pressure and hydrogenated at room temperature with stirring for 8 hours. Upon completion of the reaction, the mixture was filtered through diatomaceous earth (Cellite) to remove the catalyst. The filtrate was concentrated under reduced pressure to give a residue. To the residue was added 200 mL of isopropanol and the mixture was stirred. The precipitated solid was collected by filtration and dried to give 25.1 g of the target product 3-(2-chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one as white crystals in 90% yield.

References

[1] Patent: WO2004/35573, 2004, A1. Location in patent: Page 9
[2] Journal of the American Chemical Society, 2017, vol. 139, # 24, p. 8267 - 8276
[3] Letters in Drug Design and Discovery, 2011, vol. 8, # 10, p. 988 - 995
[4] Medicinal Chemistry, 2013, vol. 9, # 2, p. 240 - 248

3-(2-Chloroethyl)-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one(63234-80-0)Related Product Information

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