Sodium hydride → 2-(3-Chloroanilino)-4-(2-methylimidazol-5-yl)pyrimidin

HRID 1064302Notes

Reaction equation

HRID 1064302 reaction equation
[H-].[Na+].CN(C)[CH:5]=[CH:6][C:7]([C:9]1[NH:13][C:12]([CH3:14])=[N:11][CH:10]=1)=O.[Cl:16][C:17]1[CH:18]=[C:19]([NH:23][C:24]([NH2:26])=[NH:25])[CH:20]=[CH:21][CH:22]=1>C(O)CCC>[Cl:16][C:17]1[CH:18]=[C:19]([CH:20]=[CH:21][CH:22]=1)[NH:23][C:24]1[N:26]=[C:7]([C:9]2[NH:13][C:12]([CH3:14])=[N:11][CH:10]=2)[CH:6]=[CH:5][N:25]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 14770923-(dimethylamino)-1-(2-methyl-1H-imidazol-5-yl)-2-propen-1-oneHCID 178512488HCID 178512488, compound

Product 1

HCID 222734852-(3-Chloroanilino)-4-(2-methylimidazol-5-yl)pyrimidinYield 21%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Sodium hydride (45 mg of a 60% suspension in mineral oil, 1.12 mmol) was added to a stirred suspension of 5-(3-dimethylaminoprop-2-en-1-oyl)-2-methylimidazole (100 mg, 0.56 mmol) and 3-chlorophenylguanidine (95 mg, 0.56 mmol) in dry 1-butanol (4.0 ml) under nitrogen. The mixture was stirred at ambient temperature for 15 minutes then heated at 126° C. for 26 hours. The reaction mixture was allowed to cool and the volatiles were removed by evaporation. The residue was suspended in water (20 ml) and acetic acid (67 μl) was added and the solution extracted with DCM (3×20 ml). The extracts were combined, dried (NaSO4) and the solvent removed by evaporation. The residue was purified by column chromatography eluting with DCM/MeOH (100:0 increasing in polarity to 92:8) to give the title compound 33 mg, (21%) as a solid. NMR: 2.35 (s, 3H), 6.95 (d, 1H), 7.23 (d, 1M, 7.30 (t, 1H), 7.67 (s, 1H), 7.72 (s, 1H), 8.05 (s, 1H), 8.43 (d, 1H), 9.62 (s, 1H), 12.15 (s, 1H); m/z: 286.

Workup

  1. temperaturethen heated at 126° C. for 26 hours
  2. temperatureto cool
  3. customthe volatiles were removed by evaporation
  4. additionacetic acid (67 μl) was added
  5. extractionthe solution extracted with DCM (3×20 ml)
  6. dry with materialdried (NaSO4)
  7. customthe solvent removed by evaporation
  8. customThe residue was purified by column chromatography
  9. washeluting with DCM/MeOH (100:0 increasing in polarity to 92:8)

Sources & evidence

ORD record
ord-f205ec8874be4471a99b5891cec72194
Source dataset
uspto-grants-2005_11
Patent number
US06969714B2

Reaction notes

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