Dichloromethane → 2-(chloromethyl)-3-(3-fluorophenyl)-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-one hydrochloride

HRID 405959Notes

Reaction equation

HRID 405959 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13](=[O:14])[N:12]3[C:15]([CH3:19])=[CH:16][CH:17]=[CH:18][C:11]3=[N:10][C:9]=2[CH2:20]O)[CH:5]=[CH:6][CH:7]=1.O=S(Cl)[Cl:24].C(Cl)[Cl:27]>C(Cl)(Cl)Cl>[ClH:24].[Cl:27][CH2:20][C:9]1[N:10]=[C:11]2[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[N:12]2[C:13](=[O:14])[C:8]=1[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 668313583-(3-fluorophenyl)-2-(hydroxymethyl)-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

Product 1

HCID 668313822-(chloromethyl)-3-(3-fluorophenyl)-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-one hydrochloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 3-(3-fluorophenyl)-2-(hydroxymethyl)-6-methyl-4H-pyrido[1,2-a]-pyrimidin-4-one (0.7141 g, 2.512 mmol, Prepared in Example 1) in chloroform (8.373 mL) was treated with SOCl2 (0.9139 mL, 12.56 mmol) dropwise at 0° C., and the reaction mixture was allowed to warm to rt with stirring. After 1 h, the mixture was concd under reduced pressure, co-evaporated three times with DCM, and dried under high vacuum to give 2-(chloromethyl)-3-(3-fluorophenyl)-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-one hydrochloride as a brown solid: Mass Spectrum (ESI) m/e=303.0 (M+1).

Workup

  1. customdried under high vacuum

Sources & evidence

ORD record
ord-45d2b399bc414caea2908abde8e81b05
Source dataset
uspto-grants-2014_06
Patent number
US08754089B2

Reaction notes

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