Sodium ethoxide → HCID 12451282, compound

HRID 1355717Notes

Reaction equation

HRID 1355717 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](SC)[C:5]([C:10]#[N:11])=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:3]=1.[CH3:18][CH2:19][O-:20].[Na+]>C(O)C>[NH2:1][C:2]1[N:7]=[C:6]([O:20][CH2:19][CH3:18])[C:5]([C:10]#[N:11])=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:3]=1

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 12451271HCID 12451271, compound

Product 1

HCID 12451282HCID 12451282, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 0.2 g (0.86 mmol) 2-amino-4-(methylthio)-6-phenyl-5-pyrimidinecarbonitrile in 10 ml ethanol was added 0.33 ml (0.89 mmol) sodium ethylate solution (2.7M in ethanol) and the mixture heated at reflux for 2 h. The reaction mixture was then concentrated in vacuo. The residue was partitioned between water and dichloromethane and the organic phase dried over sodium sulfate and concentrated in vacuo. Chromatography (ethyl acetate/hexane 1/1) afforded 60 mg (29%) 2-amino-4-ethoxy-6-phenyl-pyrimidine-5-carbonitrile as a white crystalline solid. MS m/e (%):240 (M+, 100), 239 ([M—H]+, 50), 170 (56).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 2 h
  3. concentrationThe reaction mixture was then concentrated in vacuo
  4. customThe residue was partitioned between water and dichloromethane
  5. dry with materialthe organic phase dried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2398dd1fa0944246a06cbd825b345f65
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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