9-Benzyloxy-6-(1-naphthalen-1-yl-cyclopentylmethyl)-2-oxetan-3-yl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione → 9-hydroxy-6-(1-naphthalen-1-yl-cyclopentylmethyl)-2-oxetan-3-yl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione

HRID 2169399Notes

Reaction equation

HRID 2169399 reaction equation
C([O:8][C:9]1[C:14](=[O:15])[N:13]=[C:12]([CH2:16][C:17]2([C:22]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH:25]=[CH:24][CH:23]=3)[CH2:21][CH2:20][CH2:19][CH2:18]2)[N:11]2[CH2:32][CH2:33][N:34]([CH:37]3[CH2:40][O:39][CH2:38]3)[C:35](=[O:36])[C:10]=12)C1C=CC=CC=1>C(O)C.[Pd]>[OH:8][C:9]1[C:14](=[O:15])[N:13]=[C:12]([CH2:16][C:17]2([C:22]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH:25]=[CH:24][CH:23]=3)[CH2:21][CH2:20][CH2:19][CH2:18]2)[N:11]2[CH2:32][CH2:33][N:34]([CH:37]3[CH2:38][O:39][CH2:40]3)[C:35](=[O:36])[C:10]=12

Participants

4

Reactant 1

HCID 867260299-Benzyloxy-6-(1-naphthalen-1-yl-cyclopentylmethyl)-2-oxetan-3-yl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione

Product 1

HCID 867260309-hydroxy-6-(1-naphthalen-1-yl-cyclopentylmethyl)-2-oxetan-3-yl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dioneYield 31.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 9-benzyloxy-6-(1-naphthalen-1-yl-cyclopentylmethyl)-2-oxetan-3-yl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione (364) (125 mg, 0.23 mmol) in ethanol (60 mL) was degassed under nitrogen, followed by the addition of Pd—C (10%) (40 mg) and again degassed under nitrogen. The reaction mixture was then stirred under a hydrogen atmosphere of balloon pressure for 25 min at room temperature. The reaction mixture was the filtered through a celite bed and the filtrate was concentrated in vacuo to get a crude sticky mass which was purified by preparative TLC plate using as developing solvent 3% methanol in dichloromethane to get pure 9-hydroxy-6-(1-naphthalen-1-yl-cyclopentylmethyl)-2-oxetan-3-yl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione (365) (32 mg, 31%) as an off-white solid.

Workup

  1. customagain degassed under nitrogen
  2. filtrationfiltered through a celite bed
  3. concentrationthe filtrate was concentrated in vacuo
  4. customto get a crude sticky mass which
  5. customwas purified by preparative TLC plate

Sources & evidence

ORD record
ord-bd3fb1538a9c49588f138f5efa426e0a
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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