Sodium Methoxide → 2,5-Diamino-4-phenyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester

HRID 1355710Notes

Reaction equation

HRID 1355710 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH2:4][S:5][C:6]1[C:11]([C:12]#[N:13])=[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:9]=[C:8]([NH2:20])[N:7]=1.C[O-].[Na+]>CO>[CH3:1][O:2][C:3]([C:4]1[S:5][C:6]2[N:7]=[C:8]([NH2:20])[N:9]=[C:10]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:11]=2[C:12]=1[NH2:13])=[O:21]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 69782149(2-Amino-5-cyano-6-phenyl-pyrimidin-4-ylsulfanyl)-acetic acid methyl ester

Product 1

HCID 697820682,5-Diamino-4-phenyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl esterYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Following the method of Perez et al. (Synthesis 1983, 402), to a stirred solution of 0.27 g (0.9 mmol) (2-amino-5-cyano-6-phenyl-pyrimidin-4-ylsulfanyl)-acetic acid methyl ester in 25 ml methanol was added 0.17 ml (0.9 mmol) sodium methylate solutiuon (5.4M in methanol) and stirring continued for 16 hours at reflux. The reaction mixture was then concentrated in vacuo to ca 5 ml and the resulting crystals collected by filtration and washed with ether/methanol (10/1) to afford 0.2 g (74%) 2,5-diamino-4-phenyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester as a yellow crystalline solid. ES-MS m/e (%): 301 (M+H+, 100), 269 ([M+H-MeOH]+, 45).

Workup

  1. customthe method of Perez et al. (Synthesis 1983, 402)
  2. temperatureat reflux
  3. concentrationThe reaction mixture was then concentrated in vacuo to ca 5 ml
  4. filtrationthe resulting crystals collected by filtration
  5. washwashed with ether/methanol (10/1)

Sources & evidence

ORD record
ord-daf3dc0d8d6f4ef584cc37d20a45c6df
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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