Sodium Hydroxide → (4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)(5-((diphenylmethylene)amino)pyridin-3-yl)methanone

HRID 82257노트

반응식

HRID 82257 반응식
[Cl:1][C:2]1[C:3]2[C:10]([CH:11]([C:13]3[CH:14]=[N:15][CH:16]=[C:17]([N:19]=[C:20]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH:18]=3)[OH:12])=[CH:9][N:8]([CH3:33])[C:4]=2[N:5]=[CH:6][N:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH-].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[C:3]2[C:10]([C:11]([C:13]3[CH:14]=[N:15][CH:16]=[C:17]([N:19]=[C:20]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH:18]=3)=[O:12])=[CH:9][N:8]([CH3:33])[C:4]=2[N:5]=[CH:6][N:7]=1

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 86672118(4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)(5-((diphenylmethylene)amino)pyridin-3-yl)methanol

생성물 1

HCID 86672119(4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)(5-((diphenylmethylene)amino)pyridin-3-yl)methanone수율 99%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)(5-((diphenylmethylene)amino)pyridin-3-yl)methanol (Preparation 228, 11.4 g, 25 mmol) in CH2Cl2 (150 mL), Dess-Martin periodinane (15.9 g, 37 mmol) was added in portions. The reaction mixture was stirred at room temperature for 10 hours and then aqueous NaOH (30 mL) was added. The mixture was stirred for a further 0.5 hours. The mixture was then separated and the aqueous layer was exacted by CH2Cl2 (100 mL×2). The combined organic layers were concentrated and washed with ether to provide the title compound as a brown solid in 99% yield, 11 g.

후처리

  1. stirringThe mixture was stirred for a further 0.5 hours
  2. customThe mixture was then separated
  3. concentrationThe combined organic layers were concentrated
  4. washwashed with ether

출처 및 근거

ORD 기록
ord-0b35e63e66e446f1ba025cc8ad331e9c
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846698B2

반응 노트

불러오는 중…