Bromine → HCID 117856144, compound

HRID 1750333Notes

Reaction equation

HRID 1750333 reaction equation
[CH3:1][N:2]1[C:6]2[N:7]=[CH:8][N:9]([CH2:12][C:13]([F:16])([F:15])[F:14])[C:10](=[O:11])[C:5]=2[C:4]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)=[CH:3]1.[Br:23]Br.C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C=O)C.O>[Br:23][C:3]1[N:2]([CH3:1])[C:6]2[N:7]=[CH:8][N:9]([CH2:12][C:13]([F:15])([F:16])[F:14])[C:10](=[O:11])[C:5]=2[C:4]=1[C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 117857099HCID 117857099, compound

Product 1

HCID 117856144HCID 117856144, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

7-methyl-5-(pyridin-3-yl)-3-(2,2,2-trifluoroethyl)-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one (0.28 g, 0.908 mmol) was dissolved in DMF (8 ml). The solution was cooled down to 0° C. Bromine (0.056 ml, 1.09 mmol) was added in dropwise. After 30 min, the reaction mixture was diluted with a aqueous mixture (3:1:4 water, saturated sodium bicarbonate solution and 20% w/w sodium thiosulfate solution, 80 ml) and extracted with ethyl acetate (3×50 ml). The combined organic phase was washed with water (4×60 ml), brine and concentrated to give title compound (0.13 g, 37%). LCMS RT=0.81 min, [M+H+(79Br)]=387.0, [M+H+(81Br)]=389.0.

Workup

  1. extractionextracted with ethyl acetate (3×50 ml)
  2. washThe combined organic phase was washed with water (4×60 ml), brine
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-0191450971cc43e79626e3f3f27344d3
Source dataset
uspto-grants-2015_10
Patent number
US09156853B2

Reaction notes

Loading…