Potassium Carbonate → 2-[1-(3-chloro-5-methoxy-pyrazin-2-ylmethyl)-1H-imidazol-2-yl]-pyrimidine

HRID 1609852ノート

反応式

HRID 1609852 の反応式
[Cl:1][C:2]1[C:3]([CH2:10]Cl)=[N:4][CH:5]=[C:6]([O:8][CH3:9])[N:7]=1.[NH:12]1[CH:16]=[CH:15][N:14]=[C:13]1[C:17]1[N:22]=[CH:21][CH:20]=[CH:19][N:18]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[C:3]([CH2:10][N:12]2[CH:16]=[CH:15][N:14]=[C:13]2[C:17]2[N:18]=[CH:19][CH:20]=[CH:21][N:22]=2)=[N:4][CH:5]=[C:6]([O:8][CH3:9])[N:7]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 222603773-Chloro-2-chloromethyl-5-methoxy-pyrazineHCID 222603812-(1H-Imidazol-2-yl)pyrimidine

生成物 1

HCID 103575922-[1-(3-chloro-5-methoxy-pyrazin-2-ylmethyl)-1H-imidazol-2-yl]-pyrimidine収率 55.1%

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 3-chloro-2-chloromethyl-5-methoxy pyrazine (141 mg, 0.73 mmol), 2-(1H-imidazol-2-yl)-pyrimidine (105 mg, 0.72 mmol) and K2CO3 (307 mg, 2.22 mmol) in DMF (10 mL) is stirred at 45° C. for 16 hours. On cooling, the reaction is quenched with saturated NH4Cl (5 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 120 mg of 2-[1-(3-chloro-5-methoxy-pyrazin-2-ylmethyl)-1H-imidazol-2-yl]-pyrimidine as an oil. 1H NMR (CDCl3) 8.98 (d, 2H), 7.98 (s, 1H), 7.27 (s, 1H), 7.14–7.18 (m, 2H), 6.05 (s, 2H), 3.97 (s, 3H). H. 2-[1-(3,5-Dimethoxy-pyrazin-2-ylmethyl)-1H-imidazol-2-yl]-pyrimidine (Compound 9)

後処理

  1. temperatureOn cooling
  2. customthe reaction is quenched with saturated NH4Cl (5 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-26e53d8579d04b74809dc7cba56e8b1b
出典データセット
uspto-grants-2006_01
特許番号
US06982268B2

反応ノート

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