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

HRID 1064302노트

반응식

HRID 1064302 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 2631-Butanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-f205ec8874be4471a99b5891cec72194
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06969714B2

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