2,4-Bis-benzyloxy-6-(3-[1,3]dioxolan-2-yl-5-methyl-phenoxy)-5-isopropyl-pyrimidine → 6-(3-[1,3]Dioxolan-2-yl-5-methyl-phenoxy)-5-isopropyl-1H-pyrimidine-2,4-dione
Reaction equation
C([O:8][C:9]1[N:14]=[C:13]([O:15]CC2C=CC=CC=2)[C:12]([CH:23]([CH3:25])[CH3:24])=[C:11]([O:26][C:27]2[CH:32]=[C:31]([CH3:33])[CH:30]=[C:29]([CH:34]3[O:38][CH2:37][CH2:36][O:35]3)[CH:28]=2)[N:10]=1)C1C=CC=CC=1>C1COCC1.[Pd]>[O:38]1[CH2:37][CH2:36][O:35][CH:34]1[C:29]1[CH:28]=[C:27]([CH:32]=[C:31]([CH3:33])[CH:30]=1)[O:26][C:11]1[NH:10][C:9](=[O:8])[NH:14][C:13](=[O:15])[C:12]=1[CH:23]([CH3:25])[CH3:24]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
2,4-Bis-benzyloxy-6-(3-[1,3]dioxolan-2-yl-5-methyl-phenoxy)-5-isopropyl-pyrimidine (1.56 g, 3.04 mmol) in anhydrous THF (20 ml) was stirred in the presence of 10% palladium on carbon (58 mg) under an atmosphere of hydrogen. After 3 hr., the mixture was filtered through a celite pad and the pad was washed with methanol. The combined filtrate was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, EA:hexanes (4:1)) to afford 889 mg (89%) of a white solid. m.p. 201-203° C.; 1H NMR (200 MHz, CDCl3) δ 1.20 (6H, d, J=7.2 Hz), 2.37 (3H, s), 3.09 (1H, m), 4.02-4.15 (4H, m), 5.73 (1H, s), 6.80 (1H, s), 6.99 (1H, s), 7.16 (1H, s), 8.80 (1H, s), 9.19 (1H, s); m/z (LC/Mass, EI) 333 (M+H+).
Workup
- filtration, the mixture was filtered through a celite pad
- washthe pad was washed with methanol
- customThe combined filtrate was evaporated in vacuo
- customthe residue was purified by silica gel column chromatography (eluent, EA:hexanes (4:1))
Sources & evidence
- ORD record
- ord-0bdac28cf0854941a50aa06447841001
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08106064B2
Reaction notes
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