N-bromobutanimide → HCID 89651551, compound

HRID 515940Notes

Reaction equation

HRID 515940 reaction equation
[F:1][C@:2]1([CH3:19])[C@H:6]([OH:7])[C@@:5]([F:10])([CH2:8][OH:9])[O:4][C@H:3]1[N:11]1[CH:16]=[CH:15][C:14](=[O:17])[NH:13][C:12]1=[O:18].C1C(=O)N([Br:27])C(=O)C1>CN(C=O)C>[Br:27][C:15]1[C:14](=[O:17])[NH:13][C:12](=[O:18])[N:11]([C@H:3]2[C@@:2]([F:1])([CH3:19])[C@H:6]([OH:7])[C@@:5]([F:10])([CH2:8][OH:9])[O:4]2)[CH:16]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 89650994HCID 89650994, compound

Product 1

HCID 89651551HCID 89651551, compoundYield 104.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

In a 2 mL microwave vial, chiral 1-((2R,3R,4S,5S)-3,5-difluoro-4-hydroxy-5-(hydroxymethyl)-3-methyl-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione (70 mg, 0.252 mmol), and NBS (67.2 mg, 0.377 mmol), were dissolved in DMF (0.7 ml). The mixture was capped and heated under microwave irradiation at 80° C. for 10 min. LC/MS analysis indicated the starting material was completely consumed and the formation of the desired production as the only major product. The solvent was evaporated, and the residue was purified by a 2×4 g silica gel cartridge, eluted with 0-70% EtOAc in hexanes to provide the title compound as a white solid (94 mg, 90%)

Workup

  1. customThe mixture was capped
  2. customwas completely consumed
  3. customThe solvent was evaporated
  4. customthe residue was purified by a 2×4 g silica gel cartridge
  5. washeluted with 0-70% EtOAc in hexanes

Sources & evidence

ORD record
ord-4b9f68158ad9472ca4d8f814fc6a6dc3
Source dataset
uspto-grants-2015_08
Patent number
US09108999B2

Reaction notes

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