N-bromobutanimide → 6-Bromo-5-phenyl-3-(2,2,2-trifluoroethyl)thieno[2,3-d]pyrimidin-4(3H)-one

HRID 1750316Notes

Reaction equation

HRID 1750316 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[S:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C(=O)N([Br:29])C(=O)C1>CN(C=O)C.O>[Br:29][C:8]1[S: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

5

Reactant 2

HCID 67184N-bromobutanimideHCID 1178570375-Phenyl-3-(2,2,2-trifluoroethyl)thieno[2,3-d]pyrimidin-4(3H)-one

Product 1

HCID 1178571116-Bromo-5-phenyl-3-(2,2,2-trifluoroethyl)thieno[2,3-d]pyrimidin-4(3H)-oneYield 91.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-phenyl-3-(2,2,2-trifluoroethyl)thieno[2,3-d]pyrimidin-4(3H)-one (0.4 g, 1.29 mmol) and NBS (0.459 g, 2.58 mmol) in DMF (5 ml) was heated at 80° C. for 2 h. The reaction mixture was diluted with water (40 ml) and extracted with DCM (3×25 ml). The combined organic phases were washed with water (3×45 ml) and brine (30 ml), dried and concentrated to give the title compound (0.46 g, 91%). LCMS RT=1.46 min, M+H+=390.9/392.9.

Workup

  1. extractionextracted with DCM (3×25 ml)
  2. washThe combined organic phases were washed with water (3×45 ml) and brine (30 ml)
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-af546c77a5b1408b829d26c5d99f4d16
Source dataset
uspto-grants-2015_10
Patent number
US09156853B2

Reaction notes

Loading…