Dichloromethane → 2,4-Diamino-6-ethyl-5-(3-(6-chloroquinolin-4-yloxy)propoxy)pyrimidine

HRID 40801ノート

反応式

HRID 40801 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+].[Cl:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[N:22]=[CH:21][CH:20]=[C:19]2[O:26][CH2:27][CH2:28][CH2:29]Br.ClCCl>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:19]2[C:18]3[C:23](=[CH:24][CH:25]=[C:16]([Cl:15])[CH:17]=3)[N:22]=[CH:21][CH:20]=2)=[C:4]([CH2:10][CH3:11])[N:3]=1

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 168937Lithium hydroxide, monohydrateHCID 205093882,4-Diamino-6-ethylpyrimidin-5-olHCID 685763413-(6-Chloroquinolin-4-yloxy)propyl bromide

生成物 1

HCID 252629232,4-Diamino-6-ethyl-5-(3-(6-chloroquinolin-4-yloxy)propoxy)pyrimidine収率 55%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
25 °C

実験手順

2,4-Diamino-6-ethyl-5-hydroxypyrimidine (1.39 g, 9 mmol) was added to a stirred solution of lithium hydroxide monohydrate (1.32 g, 31.50 mmol) in DMF (5 mL) and the reaction mixture was stirred at 25° C. for 1 hour. A solution of 3-(6-chloroquinolin-4-yloxy)propyl bromide (2.71 g, 9 mmol) in DMF (3 mL) was added and the reaction mixture was left stirring at 25° C. overnight. DMF was partially removed under reduced pressure to give residue. The residue was digested with dichloromethane and filtered to give white solid. Recrystallization with aqueous methanol and hot water afforded the desired diaminopyrimidine as white solid (1.85 g, 55%, m.p. 230-231° C. (dec.)). 1H NMR (500 MHz, DMSO-d6): 0.91 (3H, t, J=7.6 Hz), 2.26 (2H, q, J=7.6 Hz), 2.31 (2H, m), 3.86 (2H, t, J=6 Hz), 4.45 (2H, t, J=5.9 Hz), 5.59 (2H, s), 6.17, (2H, s), 7.15 (1H, d, J=5.3 Hz), 7.76 (1H, dd, J=9.0, 2.4 Hz), 7.98 (1H, d, J=9.0 Hz), 8.14 (1H, d, J=2.4 Hz), 8.77 (1H, d, J=5.2 Hz).

後処理

  1. waitthe reaction mixture was left
  2. stirringstirring at 25° C. overnight
  3. customDMF was partially removed under reduced pressure
  4. customto give residue
  5. filtrationfiltered
  6. customto give white solid
  7. customRecrystallization with aqueous methanol and hot water

出典と根拠

ORDレコード
ord-4b116ecee37545d8ae00883982414f58
出典データセット
uspto-grants-2013_09
特許番号
US08530491B2

反応ノート

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