Sodium Methoxide → 2-Anilino-4-(1-methylimidazol-5-yl)pyrimidine

HRID 1064309Notes

Reaction equation

HRID 1064309 reaction equation
C[O-].[Na+].CN(C)[CH:6]=[CH:7][C:8]([C:10]1[N:14]([CH3:15])[CH:13]=[N:12][CH:11]=1)=O.C(=O)(O)O.[C:21]1([NH:27][C:28]([NH2:30])=[NH:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CC(O)C>[NH:27]([C:28]1[N:30]=[C:8]([C:10]2[N:14]([CH3:15])[CH:13]=[N:12][CH:11]=2)[CH:7]=[CH:6][N:29]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 16217093Carbonic acid, compound with phenylguanidine (1:1)HCID 69665434HCID 69665434, compound

Product 1

HCID 222734872-Anilino-4-(1-methylimidazol-5-yl)pyrimidineYield 64%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Sodium methoxide (2.63 g, 48.7 mmol) was added to a solution of 5-(3-dimethylaminoprop-2-en-1-oyl)-1-methylimidazole Method 4; 2.91 g, 16.2 mmol) and phenylguanidine hydrogen carbonate (3.52 g, 17.9 mmol) in 2-propanol (14 ml) and the reaction mixture heated at reflux for 3 hours. The reaction mixture was allowed to cool and partitioned between EtOAc and saturated aqueous sodium, hydrogen carbonate solution. The organic phase was separated, dried and the solvent removed by evaporation. The residue was purified by column chromatography eluting with DCM and 7M methanolic ammonia solution (97:3) to give the title compound 2.57 g, (64%) as a solid. M/z: 252.

Workup

  1. temperatureat reflux for 3 hours
  2. temperatureto cool
  3. custompartitioned between EtOAc and saturated aqueous sodium, hydrogen carbonate solution
  4. customThe organic phase was separated
  5. customdried
  6. customthe solvent removed by evaporation
  7. customThe residue was purified by column chromatography
  8. washeluting with DCM and 7M methanolic ammonia solution (97:3)

Sources & evidence

ORD record
ord-7a7a6b785856414cb39aa6c4e6a2a243
Source dataset
uspto-grants-2005_11
Patent number
US06969714B2

Reaction notes

Loading…