Diisopropylethylamine → 4-(6-Oxo-1,6-dihydro-pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1993401

반응식

HRID 1993401 반응식
Cl[C:2]1[N:7]=[CH:6][NH:5][C:4](=[O:8])[CH:3]=1.C(N(C(C)C)C(C)C)C.[C:18]([N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]>C(O)(CC)C>[C:21]([O:20][C:18]([N:25]1[CH2:30][CH2:29][N:28]([C:2]2[N:7]=[CH:6][NH:5][C:4](=[O:8])[CH:3]=2)[CH2:27][CH2:26]1)=[O:19])([CH3:24])([CH3:22])[CH3:23]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 1354454786-Chloropyrimidin-4-ol

생성물 1

HCID 1361025614-(6-Oxo-1,6-dihydro-pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester수율 74.1%

시약·촉매·용매 1

HCID 6568(+-)-2-Butanol용매

반응 조건

온도
80 °C

실험 절차

To a suspension of 6-chloro-3H-pyrimidin-4-one (˜0.23 mol) in sec-butanol (525 mL) was added ethyldiisopropylamine (49.7 mL, 0.3 mol) and BOC-piperazine (available from Aldrich; 55.9 g, 0.3 mol). The reaction was stirred at 80° C. for 8 hours, and then allowed to cool to room temperature. The crude reaction mixture was filtered, and washed with sec-butanol to give 4-(6-oxo-1,6-dihydro-pyrimidin-4-yl) -piperazine-1-carboxylic acid tert-butyl ester (47.8 g, 74%) LCMS Purity=100% (Rt=1.42). 1H NMR (400 MHz, CDCl3) δ 7.80 (s, 1H), 5.34 (s, 1H), 3.56-3.46 (m, 4H), 3.46-3.38 (m, 4H), 1.38 (s, 9H).

후처리

  1. temperatureto cool to room temperature
  2. customThe crude reaction mixture
  3. filtrationwas filtered
  4. washwashed with sec-butanol

출처 및 근거

ORD 기록
ord-2f222982204644f79249ebff68ab0e53
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07652013B2

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