2-Acetylthiophene → 2-Methyl-7-(2-thienyl)-pyrido[2,3-d]pyrimidine

HRID 234879Notes

Reaction equation

HRID 234879 reaction equation
[OH-].[K+].[NH2:3][C:4]1[C:9]([CH:10]=O)=[CH:8][N:7]=[C:6]([CH3:12])[N:5]=1.[C:13]([C:16]1[S:17][CH:18]=[CH:19][CH:20]=1)(=O)[CH3:14]>CO>[CH3:12][C:6]1[N:7]=[CH:8][C:9]2[CH:10]=[CH:14][C:13]([C:16]3[S:17][CH:18]=[CH:19][CH:20]=3)=[N:3][C:4]=2[N:5]=1

Participants

5

Reactant 3

HCID 69202-AcetylthiopheneHCID 14797Potassium HydroxideHCID 129047264-Amino-2-methylpyrimidine-5-carbaldehyde

Product 1

HCID 233531042-Methyl-7-(2-thienyl)-pyrido[2,3-d]pyrimidineYield 17%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1 ml of 40% strength by weight aqueous potassium hydroxide solution was added to a suspension of 2.0 g (14.6 mmol) of 4-amino-5-formyl-2-methylpyrimidine and 1.93 g. (15.3 mmol) of 2-acetylthiophene in 25 ml of methanol. The reaction mixture was then stirred for 20 hours at 20°-25° C. after which the solvent was removed After the residue had been taken up in dichloromethane, the organic phase was washed with water, dried and evaporated down. Yield: 17%; mp.: 175°-180° C.

Workup

  1. customwas removed After the residue
  2. washthe organic phase was washed with water
  3. customdried
  4. customevaporated down

Sources & evidence

ORD record
ord-7a9f5c9d3ce34332972a7aa089723b7c
Source dataset
uspto-grants-1997_01
Patent number
US05597776

Reaction notes

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