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

HRID 2169174Notes

Reaction equation

HRID 2169174 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:13][C:14]3[N:19]4[CH2:20][CH2:21][N:22]([CH:25]([CH3:27])[CH3:26])[C:23](=[O:24])[C:18]4=[C:17]([OH:28])[C:16](=[O:29])[N:15]=3)[CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1>[Pd]>[OH:28][C:17]1[C:16](=[O:29])[N:15]=[C:14]([CH2:13][C:8]2([C:5]3[CH:4]=[CH:3][CH:2]=[CH:7][CH:6]=3)[CH2:9][CH2:10][CH2:11][CH2:12]2)[N:19]2[CH2:20][CH2:21][N:22]([CH:25]([CH3:27])[CH3:26])[C:23](=[O:24])[C:18]=12

Participants

3

Reactant 1

HCID 867258266-[1-(4-chlorophenyl)-cyclopentylmethyl]-9-hydroxy-2-isopropyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione

Product 1

HCID 867258279-hydroxy-2-isopropyl-6-(1-phenyl-cyclopentylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dioneYield 54.5%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a stirred solution of 6-[1-(4-chlorophenyl)-cyclopentylmethyl]-9-hydroxy-2-isopropyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione (32-03) (350 mg, 0.842 mmol) was added 35 mg 10% Pd—C. Hydrogenation was conducted by balloon pressure at room temperature for 9 h. After completion of the reaction, the mixture was filtered over a celite bed, which was washed with methanol, followed by 10% methanol in dichloromethane. The filtrate was concentrated to a pasty mass, which was washed with ether, followed by pentane to get 9-hydroxy-2-isopropyl-6-(1-phenyl-cyclopentylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione (32-04) (175 mg, 54.5%) as a yellow solid.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe mixture was filtered over a celite bed, which
  3. washwas washed with methanol
  4. concentrationThe filtrate was concentrated to a pasty mass, which
  5. washwas washed with ether

Sources & evidence

ORD record
ord-2be84ae567df4a8b8cfa76b14e8533d6
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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