9-Benzyloxy-6-[[2-(3,4-difluorophenyl)phenyl]methyl]-2-isopropyl-3,4-dihydropyrazino[1,2-c]pyrimidine-1,8-dione → 6-[[2-(3,4-Difluorophenyl)phenyl]methyl]-9-hydroxy-2-isopropyl-3,4-dihydropyrazino-[1,2-c]pyrimidine-1,8-dione

HRID 2169241Notes

Reaction equation

HRID 2169241 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][C:26]([F:29])=[C:25]([F:30])[CH:24]=2)[N:11]2[CH2:31][CH2:32][N:33]([CH:36]([CH3:38])[CH3:37])[C:34](=[O:35])[C:10]=12)C1C=CC=CC=1>CO.[Pd]>[F:30][C:25]1[CH:24]=[C:23]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[CH2:16][C:12]2[N:11]3[CH2:31][CH2:32][N:33]([CH:36]([CH3:38])[CH3:37])[C:34](=[O:35])[C:10]3=[C:9]([OH:8])[C:14](=[O:15])[N:13]=2)[CH:28]=[CH:27][C:26]=1[F:29]

Participants

4

Reactant 1

HCID 867258909-Benzyloxy-6-[[2-(3,4-difluorophenyl)phenyl]methyl]-2-isopropyl-3,4-dihydropyrazino[1,2-c]pyrimidine-1,8-dione

Product 1

HCID 867258896-[[2-(3,4-Difluorophenyl)phenyl]methyl]-9-hydroxy-2-isopropyl-3,4-dihydropyrazino-[1,2-c]pyrimidine-1,8-dioneYield 84.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

9-Benzyloxy-6-[[2-(3,4-difluorophenyl)phenyl]methyl]-2-isopropyl-3,4-dihydropyrazino[1,2-c]pyrimidine-1,8-dione (170) (160 mg) in methanol (20 ml) was hydrogenated over 10% Pd/C (20.6 mg) at room temperature and at atmospheric pressure for 2 h. The catalyst was filtered off, the filtrate was concentrated in vacuo to give the desired product as a light yellow foam (112 mg).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-4d0658b09f4944849c6461a08b27be80
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

Loading…