Dimethylformamide dimethyl acetal → (E)-ethyl 4-(2-(dimethylamino)vinyl)-2-(methylthio)pyrimidine-5-carboxylate

HRID 41479

Reaction equation

HRID 41479 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:14])=[N:8][C:9]([S:12][CH3:13])=[N:10][CH:11]=1)=[O:5])[CH3:2].[CH3:15][N:16]([CH:18](OC)OC)[CH3:17]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:7](/[CH:14]=[CH:15]/[N:16]([CH3:18])[CH3:17])=[N:8][C:9]([S:12][CH3:13])=[N:10][CH:11]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 188208Ethyl-2-methylthio-4-methyl-5-pyrimidine carboxylate

Product 1

HCID 86657908(E)-ethyl 4-(2-(dimethylamino)vinyl)-2-(methylthio)pyrimidine-5-carboxylateYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Methyl-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester 3 (18.0 g, 84.8 mmol) was dissolved in DMF (50 mL), N,N-Dimethylformamidedimethylacetal (22.5 mL, 170 mmol) and stirred at reflux for 3 hours. Then mixture was concentrated, the residue was dissolved in TCM, washed with water, dried, filtered, and concentrated. The product was purified by crystallization from ether to yield in a colorless solid (14.0 g, 52.5 mmol, 62%).

Workup

  1. temperatureat reflux for 3 hours
  2. concentrationThen mixture was concentrated
  3. dissolutionthe residue was dissolved in TCM
  4. washwashed with water
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product was purified by crystallization from ether

Sources & evidence

ORD record
ord-dc974b9b448b4f40ae01977f5f513159
Source dataset
uspto-grants-2013_09
Patent number
US08530650B2

Linked notes

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