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

HRID 1609840노트

반응식

HRID 1609840 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
45 °C

실험 절차

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)

후처리

  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)

출처 및 근거

ORD 기록
ord-baf27c2734c3472bb4171812237f3c52
출처 데이터셋
uspto-grants-2006_01
특허 번호
US06982268B2

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