Bromine → HCID 89810065, compound

HRID 1750321Notes

Reaction equation

HRID 1750321 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:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:3]1.[Br:23]Br>CN(C=O)C>[Br:23][C:3]1[N:2]([CH3:1])[C:6]2[N:7]=[CH:8][N:9]([CH2:12][C:13]([F:14])([F:16])[F:15])[C:10](=[O:11])[C:5]=2[C:4]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 117857076HCID 117857076, compound

Product 1

HCID 89810065HCID 89810065, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of 7-methyl-5-phenyl-3-(2,2,2-trifluoroethyl)-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one (825 mg, 2.68 mmol) in anhydrous DMF (6 ml) at 0° C. was added bromine (0.152 ml, 2.95 mmol) and the mixture stirred for 30 min. The mixture was partitioned between ethyl acetate (50 ml) and an aqueous mixture (water, saturated sodium hydrogen carbonate solution and 20% w/w sodium thiosulfate solution, 3:1:4; 100 ml). The aqueous phase was separated and extracted using ethyl acetate (3×25 ml). The combined ethyl acetate fractions were washed with brine/water (1:1, 4×25 ml), dried (anhydrous sodium sulfate), filtered and reduced in vacuo. The resulting residue was purified by silica gel chromatography (gradient 0-40% ethyl acetate in cyclohexane) to afford the title compound (0.97 g, 94%). LCMS RT=1.40 min, M+H+=385.9/388.0.

Workup

  1. customThe mixture was partitioned between ethyl acetate (50 ml)
  2. customThe aqueous phase was separated
  3. extractionextracted
  4. washThe combined ethyl acetate fractions were washed with brine/water (1:1, 4×25 ml)
  5. dry with materialdried (anhydrous sodium sulfate)
  6. filtrationfiltered
  7. customThe resulting residue was purified by silica gel chromatography (gradient 0-40% ethyl acetate in cyclohexane)

Sources & evidence

ORD record
ord-aec758615bf44cf3afb93c04d888ab86
Source dataset
uspto-grants-2015_10
Patent number
US09156853B2

Reaction notes

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