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Lithium hydroxide, monohydrate → 2,4-Diamino-6-ethyl-5-(3-(2-methylquinolin-4-yloxy)propoxy)pyrimidine

HRID 40806
ノート
印刷プレビュー

反応式

HRID 40806 の反応式
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([OH:9])=[C:4]([CH2:10][CH3:11])[N:3]=1.O.[OH-].[Li+].[CH3:15][C:16]1[CH:25]=[C:24]([O:26][CH2:27][CH2:28][CH2:29]Br)[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]=1>CN(C=O)C>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([O:9][CH2:29][CH2:28][CH2:27][O:26][C:24]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=[C:16]([CH3:15])[CH:25]=2)=[C:4]([CH2:10][CH3:11])[N:3]=1
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

5

反応物 3

HCID 168937Lithium hydroxide, monohydrateHCID 205093882,4-Diamino-6-ethylpyrimidin-5-olHCID 685750213-(2-Methylquinolin-4-yloxy)propyl bromide

生成物 1

HCID 252629222,4-Diamino-6-ethyl-5-(3-(2-methylquinolin-4-yloxy)propoxy)pyrimidine収率 47%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
25 °C

実験手順

A mixture of 2,4-diamino-6-ethyl-5-hydroxypyrimidine (0.539 g, 3.5 mmol) and lithium hydroxide monohydrate (0.294 g, 7.0 mmol) in DMF (10 mL) was stirred at 25° C. for 1 hour after that 3-(2-methylquinolin-4-yloxy)propyl bromide (0.980 g, 3.5 mmol) was added to the reaction mixture and the reaction mixture was left to stir at 25° C. overnight. Two thirds of the DMF was evaporated under vacuum and the reaction mixture was poured in water, solid was separated by filtration and dried in oven at 80° C. The crude product was purified by column chromatography on silica gel (4% MeOH: 96% CH2Cl2 as eluent) to obtain title compound as light yellow solid (0.5814 g, 47%). 1H NMR (400 MHz, DMSO-d6): 0.90 (3H, t, J=7.6 Hz), 2.30 (4H, m), 2.60 (3H, s), 3.86 (2H, t, J=5.9 Hz), 4.41 (2H, t, J=5.9 Hz), 5.59 (2H, s), 6.16 (2H, s), 6.97 (1H, s), 7.46 (1H, t, J=7.7 Hz), 7.67 (1H, t, J=7.7 Hz), 7.84 (1H, d, J=8.4 Hz), 8.09 (1H, d, J=8.2 Hz).

後処理

  1. additionwas added to the reaction mixture
  2. waitthe reaction mixture was left
  3. customTwo thirds of the DMF was evaporated under vacuum
  4. additionthe reaction mixture was poured in water
  5. customsolid was separated by filtration
  6. customdried in oven at 80° C
  7. customThe crude product was purified by column chromatography on silica gel (4% MeOH: 96% CH2Cl2 as eluent)

出典と根拠

ORDレコード
ord-494b16a359284e45a63df0e673c026fc
出典データセット
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08530491B2

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