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

HRID 1064306ノート

反応式

HRID 1064306 の反応式
[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

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 887Methanol溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-c4eda35d17aa414391e683ecee4a8562
出典データセット
uspto-grants-2005_11
特許番号
US06969714B2

反応ノート

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