Bromine → HCID 117857048, compound

HRID 1750337Notes

Reaction equation

HRID 1750337 reaction equation
[F:1][C:2]([F:15])([F:14])[CH2:3][N:4]1[C:9](=[O:10])[C:8]2[CH:11]=[CH:12][S:13][C:7]=2[N:6]=[CH:5]1.[Br:16]Br>CN(C=O)C.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>[Br:16][C:12]1[S:13][C:7]2[N:6]=[CH:5][N:4]([CH2:3][C:2]([F:1])([F:14])[F:15])[C:9](=[O:10])[C:8]=2[CH:11]=1

Participants

6

Reactant 2

HCID 24408BromineHCID 89810746HCID 89810746, compound

Product 1

HCID 117857048HCID 117857048, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 24477Sodium ThiosulfateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 3-(2,2,2-trifluoroethyl)thieno[2,3-d]pyrimidin-4(3H)-one (2 g, 8.54 mmol) and bromine (0.484 ml, 9.39 mmol) in DMF (20 ml) at 0° C. was stirred for 60 min. The reaction mixture was diluted with 1:1 sodium thiosulfate (25% aqueous solution)/saturated sodium bicarbonate (aq) solution (100 ml) and extracted with ethyl acetate (100 ml). The concentrated crude product was purified by flash chromatography (0-60% ethyl acetate/cyclohexane) to give the title compound (2.5 g, 94%). LCMS RT=1.16 min, M+H+=312.9/314.9.

Workup

  1. extractionextracted with ethyl acetate (100 ml)
  2. concentrationThe concentrated crude product
  3. customwas purified by flash chromatography (0-60% ethyl acetate/cyclohexane)

Sources & evidence

ORD record
ord-7b597e1820a34b4c8dec3c45eb0312b0
Source dataset
uspto-grants-2015_10
Patent number
US09156853B2

Reaction notes

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