2-(3-Chloroanilino)-4-(1-triphenylmethylimidazol-4-yl)pyrimidine → 2-(3-Chloroanilino)-4-(imidazol-5-yl)pyrimidine

HRID 1064306노트

반응식

HRID 1064306 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:36]=[CH:37][CH:38]=1)[NH:5][C:6]1[N:11]=[C:10]([C:12]2[N:13]=[CH:14][N:15](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:16]=2)[CH:9]=[CH:8][N:7]=1>CO.Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:36]=[CH:37][CH:38]=1)[NH:5][C:6]1[N:11]=[C:10]([C:12]2[NH:13][CH:14]=[N:15][CH:16]=2)[CH:9]=[CH:8][N:7]=1

참가 물질

4

반응물 1

HCID 222735042-(3-Chloroanilino)-4-(1-triphenylmethylimidazol-4-yl)pyrimidine

생성물 1

HCID 222734742-(3-Chloroanilino)-4-(imidazol-5-yl)pyrimidine수율 75.1%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 887Methanol용매

실험 절차

A mixture of 2-(3-chloroanilino)-4-(1-triphenylmethylimidazol-4-yl)pyrimidine (Method 2; 256 mg, 0.5 mmol) in MeOH (3 ml) and 2M hydrochloric acid (1 ml) was stirred for 15 minutes. The volatiles were removed by evaporation and the residue partitioned between EtOAc and saturated aqueous sodium hydrogen carbonate solution. The organic layer was separated, dried and the solvent removed by evaporation. The residue was purified by column chromatography eluting with DCM and 7M methanolic ammonia solution (99.5:0.5 increasing in polarity to 93:7) to give the title compound 102 mg, (75%) as a solid. NMR: 6.95 (dd, 1H), 7.25-7.33 (m, 2H), 7.73 (dd, 1H), 7.81 (d, 2H), 8.06 (s, 1H), 8.46 (d, 1H), 9.68 (s, 1H), 12.48 (br s, 1H); m/z: 270.

후처리

  1. customThe volatiles were removed by evaporation
  2. customthe residue partitioned between EtOAc and saturated aqueous sodium hydrogen carbonate solution
  3. customThe organic layer was separated
  4. customdried
  5. customthe solvent removed by evaporation
  6. customThe residue was purified by column chromatography
  7. washeluting with DCM and 7M methanolic ammonia solution (99.5:0.5 increasing in polarity to 93:7)

출처 및 근거

ORD 기록
ord-c4eda35d17aa414391e683ecee4a8562
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06969714B2

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