Hydrochloric Acid → 6-(2,3-dichlorobenzyl)-9-hydroxy-2-isopropyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione

HRID 2169219Notes

Reaction equation

HRID 2169219 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]=[C:19]([Cl:23])[C:18]=2[Cl:24])[N:11]2[CH2:25][CH2:26][N:27]([CH:30]([CH3:32])[CH3:31])[C:28](=[O:29])[C:10]=12)C1C=CC=CC=1.Cl>CO>[Cl:24][C:18]1[C:19]([Cl:23])=[CH:20][CH:21]=[CH:22][C:17]=1[CH2:16][C:12]1[N:11]2[CH2:25][CH2:26][N:27]([CH:30]([CH3:32])[CH3:31])[C:28](=[O:29])[C:10]2=[C:9]([OH:8])[C:14](=[O:15])[N:13]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 867258689-benzyloxy-6-(2,3-dichlorobenzyl)-2-isopropyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione

Product 1

HCID 867258676-(2,3-dichlorobenzyl)-9-hydroxy-2-isopropyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dioneYield 96.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 9-benzyloxy-6-(2,3-dichlorobenzyl)-2-isopropyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione (134) (70 mg, 0.095 mmol) in methanol (3 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 mixture was evaporation and the residue was basified with saturated aqueous NaHCO3 solution. The mixture was extracted with 10% methanol in dichloromethane, the organic part was separated. The drying over sodium sulfate was conducted and concentration to get a crude product, which was washed with ether followed by pentene to get 6-(2,3-dichlorobenzyl)-9-hydroxy-2-isopropyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione (135) (35 mg, 61.7%) as a brown colored solid.

Workup

  1. customAfter completion of the reaction
  2. customevaporation
  3. extractionThe mixture was extracted with 10% methanol in dichloromethane
  4. customthe organic part was separated
  5. concentrationconcentration
  6. customto get a crude product, which
  7. washwas washed with ether

Sources & evidence

ORD record
ord-1178856d40bc4983b35ca92298a2c4d7
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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