Bromine → 6-Bromo-5-phenyl-3-(2,2,2-trifluoroethyl)furo[2,3-d]pyrimidin-4(3H)-one

HRID 1750314Notes

Reaction equation

HRID 1750314 reaction equation
[C:1]1([C:7]2[C:15]3[C:14](=[O:16])[N:13]([CH2:17][C:18]([F:21])([F:20])[F:19])[CH:12]=[N:11][C:10]=3[O:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:22]Br>CN(C=O)C.CCOC(C)=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>[Br:22][C:8]1[O:9][C:10]2[N:11]=[CH:12][N:13]([CH2:17][C:18]([F:19])([F:20])[F:21])[C:14](=[O:16])[C:15]=2[C:7]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 2

HCID 24408BromineHCID 1178571565-Phenyl-3-(2,2,2-trifluoroethyl)furo[2,3-d]pyrimidin-4(3H)-one

Product 1

HCID 1178569766-Bromo-5-phenyl-3-(2,2,2-trifluoroethyl)furo[2,3-d]pyrimidin-4(3H)-one

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 24477Sodium ThiosulfateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-phenyl-3-(2,2,2-trifluoroethyl)furo[2,3-d]pyrimidin-4(3H)-one (730 mg, 2.48 mmol) in DMF (10 ml) at 0° C. was added bromine (0.153 ml, 2.98 mmol). The reaction mixture was stirred at 0° C. for 1 h and then 3 h at RT. The reaction mixture was diluted with EtOAc (50 ml) and 20% w/w aq. sodium thiosulfate solution (50 ml) and the layers were separated. The organic layer was further washed with brine (2×50 ml), dried (Na2SO4) and concentrated in vacuo affording the title compound as an orange solid. LCMS RT=1.40 min, M+H+=373/375.

Workup

  1. custom3 h
  2. customat RT
  3. customthe layers were separated
  4. washThe organic layer was further washed with brine (2×50 ml)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8b221698fac343c391aef84ab6ca1de2
Source dataset
uspto-grants-2015_10
Patent number
US09156853B2

Reaction notes

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