Trimethylsilyl triflate → 2-Methyl-1-(2',3'5'-tri-o-benzoyl-beta-d-ribofuranosyl)-pyrimidin-4-one

HRID 1107651

Reaction equation

HRID 1107651 reaction equation
[CH3:1][C:2]1[NH:7][C:6](=[O:8])[CH:5]=[CH:4][N:3]=1.S([O-])([O-])(=O)=O.[NH4+].[NH4+].C(O[C@@H:20]1[O:42][C@H:41]([CH2:43][O:44][C:45](=[O:52])[C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C@@H:31]([O:32][C:33](=[O:40])[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C@H:21]1[O:22][C:23](=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=O)C.FC(F)(F)S(O[Si](C)(C)C)(=O)=O.C([O-])(O)=O.[Na+]>C[Si](N[Si](C)(C)C)(C)C.ClCCCl>[CH3:1][C:2]1[N:3]([C@@H:20]2[O:42][C@H:41]([CH2:43][O:44][C:45](=[O:52])[C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[C@@H:31]([O:32][C:33](=[O:40])[C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C@H:21]2[O:22][C:23](=[O:30])[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:4]=[CH:5][C:6](=[O:8])[N:7]=1

Participants

8

Reactant 5

HCID 65367Trimethylsilyl triflateHCID 81455beta-D-Ribofuranose, 1-acetate 2,3,5-tribenzoateHCID 2504512-Methyl-1,4-dihydropyrimidin-4-oneHCID 516892Sodium BicarbonateHCID 6097028Ammonium Sulfate

Product 1

HCID 120421992-Methyl-1-(2',3'5'-tri-o-benzoyl-beta-d-ribofuranosyl)-pyrimidin-4-one

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 13838HexamethyldisilazaneSolvent

Procedure

2-Methylpyrimidin-4-one (4.42 g, 40 mmol) and a few crystals of ammonium sulfate were refluxed in HMDS overnight. After cooling to room temperature the colorless solution was evaporated. A solution of 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribose (40 mmol, 20.18 g) in 1,2-dichloroethane (200 ml) was added to the residue. Trimethylsilyl trifluoromethanesulfonate (TMSOTfl, 9.78 g, 44 mmol) was added and the resulting clear solution was stirred at room temperature for 2 hrs. The reaction mixture was poured in to saturated NaHCO3 (300 ml) and extracted with chloroform (2×200 ml). The organic phase was evaporated to give a colorless homogeneous foam (23.04 g, 104%, pure by NMR).

Workup

  1. customwas evaporated
  2. extractionextracted with chloroform (2×200 ml)
  3. customThe organic phase was evaporated
  4. customto give a colorless homogeneous foam (23.04 g, 104%, pure by NMR)

Sources & evidence

ORD record
ord-e32df974052c4137aa24f784c1cd3829
Source dataset
uspto-grants-2000_05
Patent number
US06060592

Linked notes

Loading…