Sodium Hydroxide → N-(1-Benzyl-4-methylpiperidin-3-yl)-N-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 1853379ノート

反応式

HRID 1853379 の反応式
[OH-].[Na+].[CH2:3]([N:10]1[CH2:15][CH2:14][CH:13]([CH3:16])[CH:12]([N:17]([CH3:37])[C:18]2[C:19]3[CH:26]=[CH:25][N:24](S(C4C=CC(C)=CC=4)(=O)=O)[C:20]=3[N:21]=[CH:22][N:23]=2)[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(OCC)(=O)C>[CH2:3]([N:10]1[CH2:15][CH2:14][CH:13]([CH3:16])[CH:12]([N:17]([CH3:37])[C:18]2[C:19]3[CH:26]=[CH:25][NH:24][C:20]=3[N:21]=[CH:22][N:23]=2)[CH2:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 67010145N-(1-Benzyl-4-methylpiperidin-3-yl)-N-methyl-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

生成物 1

HCID 12084829N-(1-Benzyl-4-methylpiperidin-3-yl)-N-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine収率 93.2%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

A mixture of 50% sodium hydroxide (10 mL) and N-(1-benzyl-4-methylpiperidin-3-yl)-N-methyl-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (400 mg, 0.80 mmol, 1.00 equiv.) was stirred at about 60° C. for about 16 hours, and then was cooled to ambient temperature. Following standard extractive workup with ethyl acetate (4×10 mL), the crude residue was then purified by silica gel column chromatography (dichloromethane/methanol (10:1)) to give the title product as a yellow solid (0.25 g; yield=88%). 1H NMR (300 MHz, CDCl3) δ: 11.35 (br s, 1H), 8.30 (s, 1H), 7.20-7.40 (m, 5H), 7.06 (d, J=3.6 Hz, 1H), 6.60 (d, J=3.6 Hz, 1H), 5.20-5.30 (m, 1H), 3.66 (s, 3H), 3.48-3.65 (m, 2H), 2.85-2.98 (m, 1H), 2.60-2.85 (m, 2H), 2.30-2.45 (m, 1H), 2.12-2.30 (m, 1H), 1.60-1.92 (m, 2H), 0.98 (d, J=6.0 Hz, 3H). LC-MS: m/z=336 (M+H)+.

後処理

  1. temperaturewas cooled to ambient temperature
  2. customthe crude residue was then purified by silica gel column chromatography (dichloromethane/methanol (10:1))

出典と根拠

ORDレコード
ord-75f0010be03b4712b0d1223fb288575a
出典データセット
uspto-grants-2015_02
特許番号
US08962638B2

反応ノート

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