Potassium Carbonate → 3-Methoxy-5-phenyl-2-(2-thiazol-2-yl-imidazol-1-ylmethyl)-pyrazine

HRID 1609840ノート

反応式

HRID 1609840 の反応式
Cl[CH2:2][C:3]1[C:8]([O:9][CH3:10])=[N:7][C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:5][N:4]=1.[NH:17]1[CH:21]=[CH:20][N:19]=[C:18]1[C:22]1[S:23][CH:24]=[CH:25][N:26]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:10][O:9][C:8]1[C:3]([CH2:2][N:17]2[CH:21]=[CH:20][N:19]=[C:18]2[C:22]2[S:23][CH:24]=[CH:25][N:26]=2)=[N:4][CH:5]=[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:7]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 222603922-Chloromethyl-3-methoxy-5-phenyl-pyrazineHCID 222603952-(1H-Imidazol-2-yl)-1,3-thiazole

生成物 1

HCID 103158053-Methoxy-5-phenyl-2-(2-thiazol-2-yl-imidazol-1-ylmethyl)-pyrazine収率 61.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
45 °C

実験手順

A mixture of 2-chloromethyl-3-methoxy-5-phenyl-pyrazine (90 mg, 0.38 mmol; prepared as described above), 2-(1H-imidazol-2-yl)-thiazole (55 mg, 0.363 mmol) and K2CO3 (159 mg, 1.15 mmol) in DMF (7 mL) is stirred at 45° C. for 16 hours. On cooling, the reaction is quenched with saturated NH4Cl (3 mL) and extracted with DCM (3×15 mL). The combined organic layers are dried and solvent removed. PTLC separation (silica gel; 10% MeOH in DCM) gives 78 mg of 3-methoxy-5-phenyl-2-(2-thiazol-2-yl-imidazol-1-ylmethyl)-pyrazine as an oil. 1H NMR (CDCl3) 8.47 (s, 1H), 7.97–8.01 (m, 2H), 7.76 (d, 1H), 7.42–7.49 (m, 3H), 7.28 (d, 1H), 7.18 (s, 1H), 7.06 (s, 1H), 6.03 (s, 2H), 4.05 (s, 3H)

後処理

  1. temperatureOn cooling
  2. customthe reaction is quenched with saturated NH4Cl (3 mL)
  3. extractionextracted with DCM (3×15 mL)
  4. customThe combined organic layers are dried
  5. customsolvent removed
  6. customPTLC separation (silica gel; 10% MeOH in DCM)

出典と根拠

ORDレコード
ord-baf27c2734c3472bb4171812237f3c52
出典データセット
uspto-grants-2006_01
特許番号
US06982268B2

反応ノート

読み込み中…