4-chloro-5-iodo-7-methyl-7H-pyrrolo[2,3-d]pyrimidine → (4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)(5-((diphenylmethylene)amino)pyridin-3-yl)methanol

HRID 82256노트

반응식

HRID 82256 반응식
[Cl:1][C:2]1[C:3]2[C:10](I)=[CH:9][N:8]([CH3:12])[C:4]=2[N:5]=[CH:6][N:7]=1.[Li]CCCC.[C:18]1([C:24](=[N:31][C:32]2[CH:33]=[N:34][CH:35]=[C:36]([CH:39]=2)[CH:37]=[O:38])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1.CCCCCC>[Cl:1][C:2]1[C:3]2[C:10]([CH:37]([C:36]3[CH:35]=[N:34][CH:33]=[C:32]([N:31]=[C:24]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH:39]=3)[OH:38])=[CH:9][N:8]([CH3:12])[C:4]=2[N:5]=[CH:6][N:7]=1

참가 물질

6

반응물 3

HCID 426094624-chloro-5-iodo-7-methyl-7H-pyrrolo[2,3-d]pyrimidineHCID 866721015-((Diphenylmethylene)amino)nicotinaldehydeHCID 178418339Butyllithium

생성물 1

HCID 86672118(4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)(5-((diphenylmethylene)amino)pyridin-3-yl)methanol수율 48%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

실험 절차

To stirred solution of 4-chloro-5-iodo-7-methyl-7H-pyrrolo[2,3-d]pyrimidine (Preparation 226, 6.6 g, 22.7 mmol) in THF (130 mL) was added n-BuLi (18.2 mL of a 2.5M solution in hexane, 45 mmol) at −75° C. under N2, and the mixture was stirred for 50 min. A solution of 5-((diphenylmethylene)amino)nicotinaldehyde (Preparation 106, 6.5 g, 22.7 mmol) in dry THF (50 mL) was added and the mixture was stirred at −70° C. for 80 min. The mixture was quenched with sat. aq. NH4Cl solution and extracted with EtOAc (300 mL). The organic layer was dried (Na2SO4) and concentrated in vacuo to give the title compound as a brown solid in 48% yield, 5.2 g.

후처리

  1. stirringthe mixture was stirred at −70° C. for 80 min
  2. customThe mixture was quenched with sat. aq. NH4Cl solution
  3. extractionextracted with EtOAc (300 mL)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-76d544c1f73348b6969a4a91ef745e93
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846698B2

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