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

HRID 2169144Notes

Reaction equation

HRID 2169144 reaction equation
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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-5477df09edf04cfeaa87dde5e082b958
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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