Hydrochloric Acid → 6-biphenyl-2-ylmethyl-9-hydroxy-2-methyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione

HRID 2169144노트

반응식

HRID 2169144 반응식
C([O:8][C:9]1[C:14](=[O:15])[N:13]=[C:12]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:11]2[CH2:29][CH2:30][N:31]([CH3:34])[C:32](=[O:33])[C:10]=12)C1C=CC=CC=1.Cl>CO>[C:18]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[CH2:16][C:12]1[N:11]2[CH2:29][CH2:30][N:31]([CH3:34])[C:32](=[O:33])[C:10]2=[C:9]([OH:8])[C:14](=[O:15])[N:13]=1

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 867257979-Benzyloxy-6-biphenyl-2-ylmethyl-2-methyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione

생성물 1

HCID 867258016-biphenyl-2-ylmethyl-9-hydroxy-2-methyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione수율 24.25%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a stirred solution of 9-benzyloxy-6-biphenyl-2-ylmethyl-2-methyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione (11-01) (350 mg, 0.776 mmol) in methanol (6 mL) was added concentrated HCl (3 mL) and the reaction mixture was stirred for 5 h at room temperature. After completion of the reaction, the volume of the reaction mixture was reduced by evaporation and the resultant mixture was basified with saturated aqueous NaHCO3 solution. The mixture was extracted with 10% methanol in dichloromethane, the separated organic part was dried over sodium sulfate and concentrated to get a crude product, which was purified by prep-HPLC (ammonium acetate-methanol) to afford 6-biphenyl-2-ylmethyl-9-hydroxy-2-methyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione (12-01) (68 mg, 24.25%) as an off-white solid.

후처리

  1. customAfter completion of the reaction
  2. customthe volume of the reaction mixture was reduced by evaporation
  3. extractionThe mixture was extracted with 10% methanol in dichloromethane
  4. dry with materialthe separated organic part was dried over sodium sulfate
  5. concentrationconcentrated
  6. customto get a crude product, which
  7. customwas purified by prep-HPLC (ammonium acetate-methanol)

출처 및 근거

ORD 기록
ord-5477df09edf04cfeaa87dde5e082b958
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09045486B2

반응 노트

불러오는 중…