Water → HCID 21891803, 화합물

HRID 858081노트

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HRID 858081 반응식
Cl.[N+:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][NH2:13])=[CH:7][CH:6]=1)([O-:4])=[O:3].[CH2:14]([N:18]1[C:23](Cl)=[CH:22][C:21](=[O:25])[N:20]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[F:33])[C:19]1=[O:34])[CH2:15][CH2:16][CH3:17].C(N(CC)CC)C.O>CN1CCCC1=O>[CH2:14]([N:18]1[C:23]([NH:13][CH2:12][CH2:11][C:8]2[CH:7]=[CH:6][C:5]([N+:2]([O-:4])=[O:3])=[CH:10][CH:9]=2)=[CH:22][C:21](=[O:25])[N:20]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[F:33])[C:19]1=[O:34])[CH2:15][CH2:16][CH3:17]

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 458983Benzeneethanamine, 4-nitro-, hydrochloride (1:1)HCID 218918181-butyl-6-chloro-3-(2-fluorobenzyl)-1H-pyrimidine-2,4-dione

생성물 1

HCID 21891803HCID 21891803, 화합물수율 41.4%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

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온도
75 °C

실험 절차

A mixture of 2-(4-nitro-phenyl)-ethylamine hydrochloride salt (Fluka) (7.85 g, 38.7 mmol), 1-butyl-6-chloro-3-(2-fluorobenzyl)-1H-pyrimidine-2,4-dione (8.0 g, 25.8 mmol) and triethylamine (10.7 mL, 77 mmol) in N-methyl-pyrrolidin-2-one (200 mL) was stirred at 75° C. for 16 hours. The reaction was then mixed with water and extracted with ethyl acetate (3×). The combined ethyl acetate layers were dried (magnesium sulfate) and concentrated. Column chromatography afforded 1-butyl-3-(2-fluorobenzyl)-6-[2-(4-nitro-phenyl)-ethylamino]-1H-pyrimidine-2,4-dione (4.7 g, 41%) as a solid. 1H NMR (CDCl3, 200 MHz) δH 0.84 (t, 3H), 1.11–1.50 (m, 4H), 3.10 (t, 2H), 3.48 (m, 2H), 3.70 (t, 2H), 4.36 (t, 1H), 4.94 (t, 1H), 5.20 (s, 2H), 6.95–7.10 (m, 2H), 7.17–7.30 (m, 2H), 7.39 (d, 2H), 8.20 (d, 2H).

후처리

  1. extractionextracted with ethyl acetate (3×)
  2. dry with materialThe combined ethyl acetate layers were dried (magnesium sulfate)
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-079bf66084924f779f454b534324519e
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07148229B2

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