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 82256ノート

反応式

HRID 82256 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-76d544c1f73348b6969a4a91ef745e93
出典データセット
uspto-grants-2014_09
特許番号
US08846698B2

反応ノート

読み込み中…