2-Acetylbutyrolactone → 3-(2-Chloroethyl)-7-methoxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

HRID 466998Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([NH2:9])=[N:7][CH:8]=1.P(Cl)(Cl)([Cl:12])=O.[C:15]([CH:18]1[CH2:22][CH2:21][O:20][C:19]1=O)(=O)[CH3:16].[OH-].[NH4+]>CC1C=CC=CC=1>[Cl:12][CH2:21][CH2:22][C:18]1[C:19](=[O:20])[N:7]2[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]2=[N:9][C:15]=1[CH3:16]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 17 parts of 5-methoxy-2-pyridinamine, 61 parts of phosphoryl chloride and 348 parts of methylbenzene was stirred for 2 hours at 60° C. 18 Parts of 3-acetyl-4,5-dihydro-2(3H)-furanone were added and the reaction mixture was stirred overnight at 90° C. The whole was poured into crushed ice and treated with ammonium hydroxide. The product was extracted with trichloromethane. The extract was dried, filtered and evaporated. The residue was stirred in a mixture of hexane and ethyl acetate (50:50 by volume). The precipitated product was filtered off and dried, yielding 10 parts (30.4%) of 3-(2-chloroethyl)-7-methoxy-2-methyl-4H-pyrido-[1,2-a]pyrimidin-4-one; mp. 150° C. (intermediate 3)

Workup

stirringthe reaction mixture was stirred overnight at 90° C
additionThe whole was poured
custominto crushed ice
extractionThe product was extracted with trichloromethane
customThe extract was dried
filtrationfiltered
customevaporated
stirringThe residue was stirred in a mixture of hexane and ethyl acetate (50:50 by volume)
filtrationThe precipitated product was filtered off
customdried

Sources & evidence

ORD record: ord-053adb8535264498a764e993f27ce90f
Source dataset: uspto-grants-1992_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05158952

Reaction notes

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