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Potassium Hydroxide → N2-(1-(6-chloro-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine

HRID 2409072
ノート
印刷プレビュー

反応式

HRID 2409072 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[N:28](S(C3C=CC(C)=CC=3)(=O)=O)[CH:27]=[CH:26][C:5]2=[N:6][C:7]=1[CH:8]([NH:10][C:11]1[N:16]=[C:15]([NH:17][C:18]2[CH:22]=[C:21]([CH:23]3[CH2:25][CH2:24]3)[NH:20][N:19]=2)[CH:14]=[CH:13][N:12]=1)[CH3:9].[OH-].[K+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]2[NH:28][CH:27]=[CH:26][C:5]2=[N:6][C:7]=1[CH:8]([NH:10][C:11]1[N:16]=[C:15]([NH:17][C:18]2[CH:22]=[C:21]([CH:23]3[CH2:24][CH2:25]3)[NH:20][N:19]=2)[CH:14]=[CH:13][N:12]=1)[CH3:9]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 14797Potassium HydroxideHCID 86689873N2-(1-(6-chloro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine

生成物 1

HCID 71611845N2-(1-(6-chloro-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine収率 26%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
100 °C

実験手順

To a solution of N2-(1-(6-chloro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine (320 mg, 0.58 mmol) in methanol (5 mL) was added an aqueous solution of KOH (2 N, 5 mL). The mixture was heated at 100° C. for 3 h. The reaction mixture was quenched with a saturated NH4Cl solution and extracted with EtOAc. The extract was washed with H2O, dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude product was purified by preparative HPLC to afford 30 mg (26%) of N2-(1-(6-chloro-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine as white solid. 1H NMR (500 MHz, CD3OD): δ 11.93 (s, 1H), 11.41 (s, 1H), 9.40 (m, 1H), 7.80 (d, 2H), 7.69 (s, 1H), 6.60 (m, 2H), 6.27 (d, 2H), 5.63 (m, 1H), 1.88 (s, 1H), 1.45 (d, 3H), 0.94 (m, 2H), 0.71 (m, 2H); MS (ESI): m/z=395.1 [M+1]+.

後処理

  1. customThe reaction mixture was quenched with a saturated NH4Cl solution
  2. extractionextracted with EtOAc
  3. washThe extract was washed with H2O
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by preparative HPLC

出典と根拠

ORDレコード
ord-b56d924bed254d4cbe51f2e70ab85e9d
出典データセット
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08815877B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート