Sodium Methoxide → HCID 12862265, compound

HRID 1355723Notes

Reaction equation

HRID 1355723 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]#[N:10])=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:3]=1.[CH3:17][O-:18].[Na+]>CO>[NH2:1][C:2]1[N:7]=[C:6]([O:18][CH3:17])[C:5]([C:9]#[N:10])=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:3]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 18507370HCID 18507370, compound

Product 1

HCID 12862265HCID 12862265, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 200 mg (0.87 mmol) 2-amino-4-chloro-6-phenyl-pyrimidine-5-carbonitrile in 5 ml methanol was added 0.4 ml (2.16 mmol) sodium methylate solution (5.4 M in methanol) and the mixture heated at reflux for 16 h. 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 to afford 130 mg (66%) 2-amino-4-methoxy-6-phenyl-pyrimidine-5-carbonitrile as a light yellow crystalline solid. ES-MS m/e (%): 227 (M+H+, 100).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 16 h
  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-43056bc1817345d0a8b9346db0f1355b
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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