9-benzyloxy-2-cyclopropyl-6-(1-phenyl-cyclopentylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione → 2-cyclopropyl-9-hydroxy-6-(1-phenyl-cyclopentylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione

HRID 2169319Notes

Reaction equation

HRID 2169319 reaction equation
C([O:8][C:9]1[C:14](=[O:15])[N:13]=[C:12]([CH2:16][C:17]2([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:21][CH2:20][CH2:19][CH2:18]2)[N:11]2[CH2:28][CH2:29][N:30]([CH:33]3[CH2:35][CH2:34]3)[C:31](=[O:32])[C:10]=12)C1C=CC=CC=1>C(O)C.[Pd]>[CH:33]1([N:30]2[CH2:29][CH2:28][N:11]3[C:12]([CH2:16][C:17]4([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)[CH2:21][CH2:20][CH2:19][CH2:18]4)=[N:13][C:14](=[O:15])[C:9]([OH:8])=[C:10]3[C:31]2=[O:32])[CH2:34][CH2:35]1

Participants

4

Reactant 1

HCID 867259579-benzyloxy-2-cyclopropyl-6-(1-phenyl-cyclopentylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione

Product 1

HCID 867259582-cyclopropyl-9-hydroxy-6-(1-phenyl-cyclopentylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dioneYield 97.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 9-benzyloxy-2-cyclopropyl-6-(1-phenyl-cyclopentylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione (286) (180 mg, 0.38 mmol) in ethanol (20 mL) was degassed, Pd—C (10%) (15 mg) added and hydrogenated for 1 h. The catalyst was filtered off, washed with ethanol (3×20 mL) and dichloromethane (2×15 mL), The combined solvent was concentrated and the solid was washed with n-pentane to get pure 2-cyclopropyl-9-hydroxy-6-(1-phenyl-cyclopentylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione (287) (140 mg, 96.25%) as a white solid.

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with ethanol (3×20 mL) and dichloromethane (2×15 mL)
  3. concentrationThe combined solvent was concentrated
  4. washthe solid was washed with n-pentane

Sources & evidence

ORD record
ord-b0ca19ff3afe4faeba5ebf4c4b35430f
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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