3-Chloro-4-(3-fluorobenzyloxy)aniline → N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-1H-pyrazolo[4,3-d]pyrimidin-7-amine

HRID 1926042ノート

反応式

HRID 1926042 の反応式
CS[C:3]1[C:4]2[NH:11][N:10]=[CH:9][C:5]=2[N:6]=[CH:7][N:8]=1.[Cl:12][C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][C:19]=1[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=1)[NH2:16].Cl.N1C=CC=CC=1>CN1CCCC1=O.C(OCC)(=O)C>[Cl:12][C:13]1[CH:14]=[C:15]([NH:16][C:3]2[C:4]3[NH:11][N:10]=[CH:9][C:5]=3[N:6]=[CH:7][N:8]=2)[CH:17]=[CH:18][C:19]=1[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=1

参加物

6

反応物 3

HCID 70592633-Chloro-4-(3-fluorobenzyloxy)anilineHCID 10176127Pyridinium chlorideHCID 552958947-(methylthio)-1H-pyrazolo[4,3-d]pyrimidine

生成物 1

HCID 57597221N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-1H-pyrazolo[4,3-d]pyrimidin-7-amine収率 66%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
120 °C

実験手順

A mixture of 7-(methylthio)-1H-pyrazolo[4,3-d]pyrimidine (known compound from literature: J. Am. Chem. Soc., 1956, 78, 2418) (150 mg), 3-chloro-4-[(3-fluorobenzyl)oxy]aniline (227 mg) and pyridine hydrochloride (156 mg) in 1-methyl-2-pyrrolidone (3 mL) was stirred at 120° C. for 10 hrs. After the completion of the reaction, the mixture was diluted with ethyl acetate and washed with saturated aqueous sodium hydrogen carbonate and saturated brine. The organic layer was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography (hexane/ethyl acetate=1/3→1/10) to give the title compound (220 mg, yield 61%) as a pale-yellow solid.

後処理

  1. customAfter the completion of the reaction
  2. washwashed with saturated aqueous sodium hydrogen carbonate and saturated brine
  3. concentrationThe organic layer was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-83cb66cbe62e43e6931e15c7c12f4ff8
出典データセット
uspto-grants-2012_05
特許番号
US08178543B2

反応ノート

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