ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Pyridine → 2-(isopropylamino)-4-(5-(phenylamino)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidine-5-carbonitrile

HRID 40867
ノート
印刷プレビュー

反応式

HRID 40867 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[C:16]([C:17]#[N:18])=[CH:15][N:14]=[C:13]([NH:19][CH:20]([CH3:22])[CH3:21])[N:12]=3)=[CH:9][N:8]([S:23]([C:26]3[CH:32]=[CH:31][C:29]([CH3:30])=[CH:28][CH:27]=3)(=[O:25])=[O:24])[C:5]2=[N:6][CH:7]=1.[C:33]1(B(O)O)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.N1C=CC=CC=1>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH:20]([NH:19][C:13]1[N:12]=[C:11]([C:10]2[C:4]3[C:5](=[N:6][CH:7]=[C:2]([NH:1][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[CH:3]=3)[N:8]([S:23]([C:26]3[CH:27]=[CH:28][C:29]([CH3:30])=[CH:31][CH:32]=3)(=[O:24])=[O:25])[CH:9]=2)[C:16]([C:17]#[N:18])=[CH:15][N:14]=1)([CH3:21])[CH3:22]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 1049PyridineHCID 66827Phenylboronic AcidHCID 686682684-(5-amino-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-(isopropylamino)pyrimidine-5-carbonitrile

生成物 1

HCID 686678792-(isopropylamino)-4-(5-(phenylamino)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidine-5-carbonitrile収率 36%

試薬・触媒・溶媒 2

HCID 8895
Cupric acetate
触媒
HCID 6344Dichloromethane溶媒

実験手順

4-(5-amino-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-(isopropylamino)pyrimidine-5-carbonitrile (0.204 g, 0.455 mmol) in DCM (12 mL) was treated with phenylboronic acid (0.111 g, 0.910 mmol, 2.0 Eq), copper acetate (0.124 g, 0.682 mmol, 1.5 Eq), pyridine (0.074 mL, 0.910 mmol, 2.0 Eq) and 4 Angstrom molecular sieves (0.600 g) and the reaction was allowed to stir at room temperature for 16 hours. The reaction mixture was quenched with 4M Ammonia in MeOH (12 mL) and filtered through a plug of celite whilst washing through with further DCM/MeOH. The combined washes were evaporated to dryness and purified by column chromatography (ISCO Companion™, 12 g column, 0-100% EtOAc/Petroleum Ether) to give the title compound as a yellow solid (85 mg, 36%).

後処理

  1. customThe reaction mixture was quenched with 4M Ammonia in MeOH (12 mL)
  2. filtrationfiltered through a plug of celite
  3. washwhilst washing through with further DCM/MeOH
  4. customThe combined washes were evaporated to dryness
  5. custompurified by column chromatography (ISCO Companion™, 12 g column, 0-100% EtOAc/Petroleum Ether)

出典と根拠

ORDレコード
ord-14400997e8ed475185fa46b5b443ac7d
出典データセット
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08530489B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート