9-Benzyloxy-6-(2-cyclohex-1-enyl-benzyl)-2-isopropyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione → 6-(2-cyclohexyl-benzyl)-9hydroxy-2-isopropyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione

HRID 2169229Notes

Reaction equation

HRID 2169229 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[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]=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>CO.[Pd]>[CH:23]1([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[CH2:16][C:12]2[N:11]3[CH2:29][CH2:30][N:31]([CH:34]([CH3:36])[CH3:35])[C:32](=[O:33])[C:10]3=[C:9]([OH:8])[C:14](=[O:15])[N:13]=2)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]1

Participants

4

Reactant 1

HCID 867258769-Benzyloxy-6-(2-cyclohex-1-enyl-benzyl)-2-isopropyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione

Product 1

HCID 867258776-(2-cyclohexyl-benzyl)-9hydroxy-2-isopropyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dioneYield 82.72%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of 9-benzyloxy-6-(2-cyclohex-1-enyl-benzyl)-2-isopropyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione (156) (170 mg, 0.352 mmol) in methanol (20 mL) was added Pd/C(10%) (170 mg) and hydrogenated under balloon pressure for 2 h at room temperature. After completion of the reaction, the mixture was filtered through a celite pad, washed with methanol (30 mL), evaporated under reduced pressure to get a crude product which was purified by preparative HPLC to get 6-(2-cyclohexyl-benzyl)-9hydroxy-2-isopropyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione (157) (115 mg, 82.72%) as an off-white solid.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe mixture was filtered through a celite pad
  3. washwashed with methanol (30 mL)
  4. customevaporated under reduced pressure
  5. customto get a crude product which
  6. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-721e714e2bee473ab3af5407b1087274
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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