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

HRID 40801노트

반응식

HRID 40801 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
25 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4b116ecee37545d8ae00883982414f58
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530491B2

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