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
反応式
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]=12参加物
4
反応物 1
生成物 1
試薬・触媒・溶媒 2
実験手順
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.