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

HRID 2169297
Notes
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Reaction equation

HRID 2169297 reaction equation
C([O:8][C:9]1[C:14](=[O:15])[N:13]=[C:12]([CH2:16][C:17]2([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[N:11]2[CH2:29][CH2:30][N:31]([CH:34]([CH3:36])[CH3:35])[C:32](=[O:33])[C:10]=12)C1C=CC=CC=1.Cl>CO>[OH:8][C:9]1[C:14](=[O:15])[N:13]=[C:12]([CH2:16][C:17]2([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]2)[N:11]2[CH2:29][CH2:30][N:31]([CH:34]([CH3:36])[CH3:35])[C:32](=[O:33])[C:10]=12
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 867259429-benzyloxy-2-isopropyl-6-(1-phenyl-cyclohexylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione

Product 1

HCID 867259439-hydroxy-2-isopropyl-6-(1-phenyl-cyclohexylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dioneYield 48%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the stirred solution of 9-benzyloxy-2-isopropyl-6-(1-phenyl-cyclohexylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione (259) (0.18 g, 0.37 mmol) in methanol (5.0 mL) was added concentrated HCl (5.0 mL) and the reaction mixture was stirred at room temperature for 3 h. After completion of the reaction, the solvent was reduced and the crude product was extracted with 10% methanol in dichloromethane. The organic part was washed with saturated NaHCO3 solution, separated and dried over Na2SO4. After evaporation, the crude product was purified by nor mal silica gel column chromatography (using 3% methanol in dichloromethane) to get 9-hydroxy-2-isopropyl-6-(1-phenyl-cyclohexylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione (260) (70.0 mg, 48.0%) as a white solid.

Workup

  1. customAfter completion of the reaction
  2. extractionthe crude product was extracted with 10% methanol in dichloromethane
  3. washThe organic part was washed with saturated NaHCO3 solution
  4. customseparated
  5. dry with materialdried over Na2SO4
  6. customAfter evaporation
  7. customthe crude product was purified by nor mal silica gel column chromatography (using 3% methanol in dichloromethane)

Sources & evidence

ORD record
ord-534f5c995a704ad3bd38e449671cb024
Source dataset
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09045486B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes