Methyl chloroacetate → (2-Amino-5-cyano-6-phenyl-pyrimidin-4-ylsulfanyl)-acetic acid methyl ester

HRID 1355708Notes

Reaction equation

HRID 1355708 reaction equation
[NH2:1][C:2]1[NH:3][C:4](=[S:16])[C:5]([C:14]#[N:15])=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1.C[O-].[Na+].Cl[CH2:21][C:22]([O:24][CH3:25])=[O:23]>CO>[CH3:25][O:24][C:22](=[O:23])[CH2:21][S:16][C:4]1[C:5]([C:14]#[N:15])=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=[C:2]([NH2:1])[N:3]=1

Participants

5

Reactant 3

HCID 7295Methyl chloroacetateHCID 10942334Sodium MethoxideHCID 178509378HCID 178509378, compound

Product 1

HCID 69782149(2-Amino-5-cyano-6-phenyl-pyrimidin-4-ylsulfanyl)-acetic acid methyl esterYield 32%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Following the method of Perez et al. (Synthesis 1983, 402), to a stirred solution of 1.0 g (4.4 mmol) 2-amino-4-phenyl-6-thioxo-1,6-dihydro-pyrimidine-5-carbonitrile in 50 ml methanol were added 1.0 ml (5.4 mmol) sodium methylate solution (5.4M in methanol) and 0.39 ml (4.4 mmol) methyl chloroacetate and stirring continued for 3 hours at reflux. The reaction mixture was then concentrated in vacuo and the residue partitioned between ethyl acetate and water. The organic phase was dried over sodium sulfate and concentrated in vacuo. Chromatography (1/1 ethyl acetate/hexane) followed by trituration in 8/1 ethyl acetate/methanol afforded 0.41 g (32%) (2-Amino-5-cyano-6-phenyl-pyrimidin-4-ylsulfanyl)-acetic acid methyl ester as a light yellow crystalline solid. EI-MS m/e (%): 300 (M+, 38), 299 ([M—H]+, 100), 241 (74), 240 (50).

Workup

  1. customthe method of Perez et al. (Synthesis 1983, 402)
  2. temperatureat reflux
  3. concentrationThe reaction mixture was then concentrated in vacuo
  4. customthe residue partitioned between ethyl acetate and water
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a98ade0baa7c454e82248f57394900d9
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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