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

HRID 40806
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HRID 40806 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+].[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
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참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
25 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-494b16a359284e45a63df0e673c026fc
출처 데이터셋
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08530491B2

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