(Diethylamino)sulfur trifluoride → 1-((2R,3R,4R,5R)-4-(benzyloxy)-5-(benzyloxymethyl)-5-(difluoromethyl)-3-fluoro-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

HRID 2205189Notes

Reaction equation

HRID 2205189 reaction equation
C(N(S(F)(F)[F:7])CC)C.[CH2:10]([O:17][C@@H:18]1[C@:22]([CH2:26][O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([CH:23]([F:25])[F:24])[O:21][C@@H:20]([N:35]2[CH:40]=[CH:39][C:38](=[O:41])[NH:37][C:36]2=[O:42])[C@H:19]1O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C1COCC1>[CH2:10]([O:17][C@@H:18]1[C@:22]([CH2:26][O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([CH:23]([F:25])[F:24])[O:21][C@@H:20]([N:35]2[CH:40]=[CH:39][C:38](=[O:41])[NH:37][C:36]2=[O:42])[C@@H:19]1[F:7])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 1182943391-((2R,3S,4S,5R)-4-(Benzyloxy)-5-((benzyloxy)methyl)-5-(difluoromethyl)-3-hydroxytetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 1182942631-((2R,3R,4R,5R)-4-(benzyloxy)-5-(benzyloxymethyl)-5-(difluoromethyl)-3-fluoro-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dioneYield 46.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Diethylaminosulfur trifluoride (7.6 g, 47.4 mmol) was added to a suspension of compound 34 (1.5 g, 3.16 mmol) in dry THF (150 mL). The mixture was stirred at 60° C. for 16 h and then cooled to room temperature. The mixture was quenched by the addition of saturated aqueous NaHCO3 solution and then extracted with ethyl acetate. The organic phase was washed with brine, dried (Na2SO4) and evaporated to dryness under reduced pressure. Purification by silica gel chromatography [petroleum ether:ethyl acetate (4:1)] afforded 39 as a brown solid (700 mg, 46%). LC-MS (M+H)+=477.4

Workup

  1. temperaturecooled to room temperature
  2. customThe mixture was quenched by the addition of saturated aqueous NaHCO3 solution
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated to dryness under reduced pressure
  7. customPurification by silica gel chromatography [petroleum ether:ethyl acetate (4:1)]

Sources & evidence

ORD record
ord-9761056fa149470eb32c13013911d9ca
Source dataset
uspto-grants-2016_06
Patent number
US09370569B2

Reaction notes

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