Benzyl Bromide → 5-Acetyl-1,3-dibenzyluracil

HRID 1297143노트

반응식

HRID 1297143 반응식
[C:1]([C:4]1[C:5](=O)[NH:6][C:7](=[O:10])[NH:8][CH:9]=1)(=[O:3])[CH3:2].[C:12](=[O:15])([O-])[O-].[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C=O)C>[C:1]([C:4]1[C:12](=[O:15])[N:8]([CH2:9][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:7](=[O:10])[N:6]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:5]=1)(=[O:3])[CH3:2]

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 2345815-Acetyluracil

생성물 1

HCID 116744085-Acetyl-1,3-dibenzyluracil수율 79.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A suspension of 5-acetyluracil (3.1 g, 20 mmol), and potassium carbonate (6.9 g, 50 mmol) in DMF (75 ml) was stirred for 20 min. Then benzyl bromide (6.0 ml, 50 mmol) was added. The resulting mixture was stirred for 8 h at room temperature. DMF was distilled under vacuum. The residue was purified by column (dichloromethane:methanol 40:1). The appropriate fraction was concentrated and crystallized from ethanol to afford 5.34 g of a white solid. Yield was 79.8%. Mp. 92-93° C. 1HNMR (CDCl3): 8.23 (s, 1H), 7.29-7.49 (m, 10H), 5.17 (s, 2H), 5.01 (s, 2H), 2.62 (s, 3H). 13CNMR (CDCl3): 194.5, 160.7, 151.0, 148.4, 136.2, 134.4, 129.2, 129.0, 128.9, 128.5, 128.2, 127.8, 112.2, 53.4, 44.9, 30.7. FAB-HRMS: [M+H]+ calcd. for C20H19N2O3 335.1396, found 335.1412.

후처리

  1. stirringThe resulting mixture was stirred for 8 h at room temperature
  2. distillationDMF was distilled under vacuum
  3. customThe residue was purified by column (dichloromethane:methanol 40:1)
  4. concentrationThe appropriate fraction was concentrated
  5. customcrystallized from ethanol

출처 및 근거

ORD 기록
ord-8574972df5a543168d5832c78c16e4fc
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07250421B2

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