Dimethylformamide dimethyl acetal → HCID 67261197, compound

HRID 2359023Notes

Reaction equation

HRID 2359023 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7](=[O:17])[CH2:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([S:15][CH3:16])[N:10]=2)=[CH:4][CH:3]=1.CO[CH:20](OC)[N:21]([CH3:23])[CH3:22]>>[CH3:20][N:21]([CH3:23])[CH:22]=[C:8]([C:9]1[CH:14]=[CH:13][N:12]=[C:11]([S:15][CH3:16])[N:10]=1)[C:7]([C:5]1[S:6][C:2]([Cl:1])=[CH:3][CH:4]=1)=[O:17]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 67257923HCID 67257923, compound

Product 1

HCID 67261197HCID 67261197, compoundYield 86%

Procedure

A solution of 1-(5-chloro-2-thienyl)-2-[2-(methylsulfanyl)pyrimidin-4-yl]ethanone (1 eq, 104 mmol) in 290 mL N,N-dimethylformamide dimethyl acetal was stirred at 80° C. for 1 h40 min and then stirred overnight at room temperature. The solvent was evaporated under reduced pressure and the residue was purified by chromatography on silica gel (heptane/ethyl acetate 1:1 to 3:7) to afford 32.7 g (86% yield) of 3-(dimethylamino)-1-(5-chloro-2-thienyl)-2-[2-(methylsulfanyl)pyrimidin-4-yl]prop-2-en-1-one.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by chromatography on silica gel (heptane/ethyl acetate 1:1 to 3:7)

Sources & evidence

ORD record
ord-24a7a374b4a9434cbe6bbf6666257aa3
Source dataset
uspto-grants-2014_04
Patent number
US08685974B2

Reaction notes

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