Water → HCID 178524912, 화합물

HRID 2169207노트

반응식

HRID 2169207 반응식
C([O:5][C:6]([C:8]1[NH:9][C:10]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Br:30])=[N:11][C:12](=[O:22])[C:13]=1[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:7])(C)(C)C.[Li+].[OH-].O>O1CCCC1>[CH2:15]([O:14][C:13]1[C:12](=[O:22])[N:11]=[C:10]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Br:30])[NH:9][C:8]=1[C:6]([OH:7])=[O:5])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 178450868HCID 178450868, 화합물

생성물 1

HCID 178524912HCID 178524912, 화합물수율 90.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

5-(Benzyloxy)-2-(2-bromobenzyl)-6-oxo-3,6-dihydro-pyrimidine-4-carboxylic acid tert-butyl ester (67) (2.69 g, 5.71 mmol, Eq: 1.00) and LiOH (683 mg, 28.5 mmol, Eq: 5) were stirred in tetrahydrofuran (18 ml)/water (9.00 ml) under reflux for 6 h, at room temperature overnight and again to reflux for 3 h. Then the solvent was mostly removed. The remaining oil was diluted with water and extracted with ethyl acetate. The aqueous layer was cooled in an ice bath and was acidified with HCl conc. Precipitate formed, was collected by filtration, washed with water and dried to afford 5-(benzyloxy)-2-(2-bromobenzyl)-6-oxo-3,6-dihydro-pyrimidine-4-carboxylic acid (68) (2.14 g, 5.15 mmol, 90.3% yield) as a white solid.

후처리

  1. temperatureagain to reflux for 3 h
  2. customThen the solvent was mostly removed
  3. additionThe remaining oil was diluted with water
  4. extractionextracted with ethyl acetate
  5. temperatureThe aqueous layer was cooled in an ice bath
  6. customformed
  7. filtrationwas collected by filtration
  8. washwashed with water
  9. customdried

출처 및 근거

ORD 기록
ord-98aa5b95e67f46898c0d883550957e35
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09045486B2

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