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

HRID 2252777노트

반응식

HRID 2252777 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-143e975fbc15488ca0a1b69df6799f99
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07323469B2

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