Dimethylformamide dimethyl acetal → (E)-3-(dimethylamino)-1-(2-(methylthio)pyrimidin-4-yl)prop-2-en-1-one

HRID 2214775Notes

Reaction equation

HRID 2214775 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([C:9](=[O:11])[CH3:10])[CH:6]=[CH:5][N:4]=1.CO[CH:14](OC)[N:15]([CH3:17])[CH3:16]>>[CH3:14][N:15]([CH3:17])/[CH:16]=[CH:10]/[C:9]([C:7]1[CH:6]=[CH:5][N:4]=[C:3]([S:2][CH3:1])[N:8]=1)=[O:11]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 116583481-[2-(Methylsulfanyl)pyrimidin-4-yl]ethan-1-one

Product 1

HCID 21948442(E)-3-(dimethylamino)-1-(2-(methylthio)pyrimidin-4-yl)prop-2-en-1-one

Procedure

A solution of 1-[2-(methylthio)pyrimidin-4-yl]ethanone (1-3, 300 mg) in N,N-dimethylformamide dimethyl acetal (10 mL) was heated at 85° C. for16 hours. The mixture was concentrated to give (2E)-3-(dimethylamino)-1-[2-(methylthio)pyrimidin-4-yl]prop-2-en-1-one (1-4) as a yellow oil which crystallized upon standing. LRMS m/z: Calc'd for C10H14N3OS (M+H) 224.1. found 224.0.

Workup

  1. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-a0ce547ea63249128488fc157b0b6cc2
Source dataset
uspto-grants-2006_09
Patent number
US07109204B2

Reaction notes

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