Thionyl Chloride → (3-Chloro-benzyl)-[6-(4-chloromethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine

HRID 133042ノート

反応式

HRID 133042 の反応式
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:7]=[C:8]([CH:28]=[CH:29][CH:30]=1)[CH2:9][NH:10][C:11]1[C:12]2[CH:19]=[C:18]([C:20]3[CH:25]=[CH:24][C:23]([CH2:26]O)=[CH:22][CH:21]=3)[NH:17][C:13]=2[N:14]=[CH:15][N:16]=1>C1(C)C=CC=CC=1>[Cl:5][C:6]1[CH:7]=[C:8]([CH:28]=[CH:29][CH:30]=1)[CH2:9][NH:10][C:11]1[C:12]2[CH:19]=[C:18]([C:20]3[CH:25]=[CH:24][C:23]([CH2:26][Cl:3])=[CH:22][CH:21]=3)[NH:17][C:13]=2[N:14]=[CH:15][N:16]=1

参加物

4

反応物 2

HCID 24386Thionyl ChlorideHCID 69179539{4-[4-(3-Chloro-benzylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-phenyl}-methanol

生成物 1

HCID 69179730(3-Chloro-benzyl)-[6-(4-chloromethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
0 °C

実験手順

A solution of 0.79 ml (10 mmol) thionylchloride in 5.5 ml of toluene is cooled to −10° C. Solid {4-[4-(3-chloro-benzylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-phenyl}-methanol is added and the suspension stirred at 0° C. for 2 h and then at RT for 17 h. The solid is filtered off, washed with toluene and suspended in water (3 ml). The mixture is treated with saturated sodium bicarbonate solution (3 ml) and stirred for 10 min. The crystals are collected by filtration washed with water, a small amount of ethanol and ether and dried to give the title compound; m.p. decomposition ˜300° C.; Rf (dichloromethane/methanol/conc. ammonia 90:10:1)=0.61; MS-ES+: (M+H)+=383.

後処理

  1. waitat RT for 17 h
  2. filtrationThe solid is filtered off
  3. washwashed with toluene
  4. additionThe mixture is treated with saturated sodium bicarbonate solution (3 ml)
  5. stirringstirred for 10 min
  6. filtrationThe crystals are collected by filtration
  7. washwashed with water
  8. dry with materiala small amount of ethanol and ether and dried

出典と根拠

ORDレコード
ord-d08da139dcb545968319e65a95186ef6
出典データセット
uspto-grants-2008_06
特許番号
US07390805B2

反応ノート

読み込み中…