2-Morpholinoethanol → 2-morpholinoethyl N-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]carbamate

HRID 51546ノート

反応式

HRID 51546 の反応式
[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:26])[O:19][C:20]4[CH:25]=CC=CC=4)=[C:13]([O:27][CH3:28])[CH:12]=3)=[CH:9][N:8]([CH:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)[C:4]=2[N:5]=[CH:6][N:7]=1.[O:35]1[CH2:40][CH2:39][N:38](CCO)[CH2:37][CH2:36]1>N1C=CC=CC=1>[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:26])[O:19][CH2:20][CH2:25][N:38]4[CH2:39][CH2:40][O:35][CH2:36][CH2:37]4)=[C:13]([O:27][CH3:28])[CH:12]=3)=[CH:9][N:8]([CH:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)[C:4]=2[N:5]=[CH:6][N:7]=1

参加物

4

反応物 2

HCID 611632-MorpholinoethanolHCID 22736249phenyl N-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]carbamate

生成物 1

HCID 227362662-morpholinoethyl N-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]carbamate

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
100 °C

実験手順

Phenyl N-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]carbamate (25 mg, 0.054 mmol) was mixed with 2-morpholino-1-ethanol (0.1 mL) in pyridine (0.7 mL). The reaction mixture was heated at 100° C. overnight. The solvent was removed and the residue was purified by preparative reverse phase HPLC to give 2-morpholinoethyl N-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]carbamate (24 mg, 0.048 mmol). The solid was dissolved in ethyl acetate (2 mL) and 1.0N HCl in ether (0.2 mL) was added slowly. The precipitate was collected through filtration under nitrogen to give 2-morpholinoethyl N-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]carbamate hydrochloride (24 mg, 0.045 mmol). 1H NMR (DMSO-d6) δ 1.88(m, 2H), 2.16(m, 2H), 3.55(m, 8H), 3.90(s, 3H), 4.03 (m, 4H), 4.49(m, 2H), 4.92(m, 1H), 7.07(m, 1H), 7.15(s, 1H), 7.65(bs, 2H), 7.84(s, 1H), 8.45(s, 1H), 8.75(s, 1H) 10.95(bs, 1H). LC/MS MH+=497.

後処理

  1. customThe solvent was removed
  2. customthe residue was purified by preparative reverse phase HPLC

出典と根拠

ORDレコード
ord-15197585ccc7498484c65b3507863163
出典データセット
uspto-grants-2004_03
特許番号
US06713474B2

反応ノート

読み込み中…