(E)-ethyl 4-(2-(dimethylamino)vinyl)-2-(methylthio)pyrimidine-5-carboxylate → 2-(methylsulfanyl)-5H,6H-pyrido(4,3-d)pyrimidin-5-one

HRID 41480Notes

Reaction equation

HRID 41480 reaction equation
C([O:3][C:4]([C:6]1[C:7](/[CH:14]=[CH:15]/[N:16](C)C)=[N:8][C:9]([S:12][CH3:13])=[N:10][CH:11]=1)=O)C>CN(C=O)C>[CH3:13][S:12][C:9]1[N:10]=[CH:11][C:6]2[C:4](=[O:3])[NH:16][CH:15]=[CH:14][C:7]=2[N:8]=1

Participants

3

Reactant 1

HCID 86657908(E)-ethyl 4-(2-(dimethylamino)vinyl)-2-(methylthio)pyrimidine-5-carboxylate

Product 1

HCID 451062072-(methylsulfanyl)-5H,6H-pyrido(4,3-d)pyrimidin-5-oneYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-((E)-2-Dimethylamino-vinyl)-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester 5 (13.5 g, 50.5 mmol) and NH4OAc (38.9 g, 505 mmol) were dissolved in DMF (250 mL) and stirred at reflux for about four days. Then mixture was concentrated, residue dissolved in TCM, washed with water, dried, filtered, and concentrated. The product was purified by crystallization from ethanol to obtain a colorless solid (7.60 g, 39.4 mmol, 78%).

Workup

  1. temperatureat reflux for about four days
  2. concentrationThen mixture was concentrated
  3. dissolutionresidue dissolved in TCM
  4. washwashed with water
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product was purified by crystallization from ethanol

Sources & evidence

ORD record
ord-b3aeae58d9f44217b5c0a19c9d2b47cc
Source dataset
uspto-grants-2013_09
Patent number
US08530650B2

Reaction notes

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