Dimethylformamide dimethyl acetal → HCID 67262224, compound

HRID 2359025Notes

Reaction equation

HRID 2359025 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7](=[O:19])[CH2:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][CH:16]([CH3:18])[CH3:17])[N:10]=2)=[CH:4][CH:3]=1.CO[CH:22](OC)[N:23]([CH3:25])[CH3:24]>CN(C)C=O>[CH3:22][N:23]([CH3:25])[CH:24]=[C:8]([C:9]1[CH:14]=[CH:13][N:12]=[C:11]([NH:15][CH:16]([CH3:17])[CH3:18])[N:10]=1)[C:7]([C:5]1[S:6][C:2]([Cl:1])=[CH:3][CH:4]=1)=[O:19]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 67258207HCID 67258207, compound

Product 1

HCID 67262224HCID 67262224, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of 1-(5-chloro-2-thienyl)-2-[2-(isopropylamino)pyrimidin-4-yl]ethanon (1 eq, 13.5 mmol) in 6 mL N,N-dimethylformamide, was added of N,N-dimethylformamide dimethyl acetal (3.4 eq, 46 mmol). The mixture was stirred at 100° C. for 2 h and then allowed to cool to room temperature. The solvent was evaporated to afford 4.5 g (95% yield) of 3-(dimethylamino)-1-(5-chloro-2-thienyl)-2-[2-(isopropylamino)pyrimidin-4-yl]prop-2-en-1-one which was used in the next step without further purification.

Workup

  1. temperatureto cool to room temperature
  2. customThe solvent was evaporated

Sources & evidence

ORD record
ord-aa5fa97ea50f438d9bfa33975a3fee1e
Source dataset
uspto-grants-2014_04
Patent number
US08685974B2

Reaction notes

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