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

HRID 1993402

반응식

HRID 1993402 반응식
Cl[C:2]1[N:7]=[CH:6][NH:5][C:4](=[O:8])[CH:3]=1.[N:9]1([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.C(N(C(C)C)CC)(C)C>CC(O)CC>[CH2:18]([O:17][C:15]([N:9]1[CH2:14][CH2:13][N:12]([C:2]2[N:7]=[CH:6][NH:5][C:4](=[O:8])[CH:3]=2)[CH2:11][CH2:10]1)=[O:16])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 643495Benzyl piperazine-1-carboxylateHCID 1354454786-Chloropyrimidin-4-ol

생성물 1

HCID 1361025684-(6-Oxo-1,6-dihydro-pyrimidin-4-yl)-piperazine-1-carboxylic acid benzyl ester수율 83%

시약·촉매·용매 1

HCID 6568(+-)-2-Butanol용매

실험 절차

A mixture of 6-chloro-3H-pyrimidin-4-one (36984-063-A; 3.90 g, 29.9 mmol), benzyl 1-piperaz-inecarboxylate (Aldrich; 8.81 g, 40.0 mmol), and diisopropylethylamine (7.0 mL, 40.2 mmol) in 2-butanol (100 mL) was heated in a 250 mL round-bottomed flask equipped with a reflux condenser in an oil-bath at about 80° C. (oil-bath temperature) for 8 hours. The heating bath was removed and the reaction mixture was left standing at room temperature overnight. The white solid was filtered off, washed with 2-butanol, and air-dried to give 4-(6-oxo-1,6-dihydro-pyrimidin-4-yl)-piperazine-1-carboxylic acid benzyl ester (7.76 g, 83%) as a white powder, mp 247-249° C. 1H NMR (d6-DMSO) δ 1.39 (s, 9H), 3.45-3.50 (m, 8H), 5.08 (s, 2H), 5.26 (s, 1H), 7.28-7.38 (m, 5H), 7.90 (s, 1H), 11.66 (br s, 1H).

후처리

  1. temperaturewas heated in a 250 mL round-bottomed flask
  2. customequipped with a reflux condenser in an oil-bath at about 80° C. (oil-bath temperature) for 8 hours
  3. customThe heating bath was removed
  4. waitthe reaction mixture was left
  5. filtrationThe white solid was filtered off
  6. washwashed with 2-butanol
  7. customair-dried

출처 및 근거

ORD 기록
ord-61c2ab1c8f2748dbaccc63c5ddf06458
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07652013B2

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