Bromine → HCID 117856774, compound

HRID 1750331Notes

Reaction equation

HRID 1750331 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][N: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:15])([F:16])[F:14])[C:10](=[O:11])[C:5]=2[C:4]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1

Participants

4

Reactant 2

HCID 24408Bromine2×HCID 117856975HCID 117856975, compound

Product 1

HCID 117856774HCID 117856774, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 7-methyl-5-(pyridin-2-yl)-3-(2,2,2-trifluoroethyl)-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one (53.6 mg, 0.174 mmol) in anhydrous DMF (1.8 ml) at 0° C. was added bromine (9.85 μl, 0.191 mmol) and the mixture stirred for 5 min. Further bromine (9.85 μl, 0.191 mmol) was added and the mixture stirred for 5 min. The mixture was partitioned between ethyl acetate (5 ml) and an aqueous mixture (3:1:4, water, saturated sodium hydrogen carbonate (aq) solution and 20% w/w sodium thiosulfate (aq) solution, 20 ml). The aqueous phase was separated and extracted with ethyl acetate (3×5 ml). The combined ethyl acetate fractions were washed with brine/water (1:1, 4×5 ml), dried (anhydrous sodium sulfate), filtered and reduced in vacuo. The resulting residue was purified by silica gel chromatography (0-5% methanol in ethyl acetate) to afford the title compound (46.8 mg, 70%). LCMS RT=0.74 min, [M+H+(79Br)]=387.0, [M+H+(81Br)]=389.0.

Workup

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

Sources & evidence

ORD record
ord-4f1ffc3544094c0781c90a70259ea061
Source dataset
uspto-grants-2015_10
Patent number
US09156853B2

Reaction notes

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