Bromine → HCID 117856778, compound

HRID 1750335Notes

Reaction equation

HRID 1750335 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][N: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:15])([F:16])[F:14])[C:10](=[O:11])[C:5]=2[C:4]=1[C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 117857366HCID 117857366, compound

Product 1

HCID 117856778HCID 117856778, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 7-methyl-5-(pyridin-4-yl)-3-(2,2,2-trifluoroethyl)-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one (130 mg, 0.422 mmol) in DMF (6 ml) was cooled to 0° C. Bromine (0.026 ml, 0.506 mmol) was added dropwise. The resulting mixture was stirred at 0° C. for 60 min. The reaction mixture was partitioned between ethyl acetate (40 ml) and a mixture of aqueous (3:1:4, water, sodium bicarbonate solution and 20% w/w sodium thiosulfate solution, 40 ml). The organic phase was separated and washed with water (3×30 ml), brine and concentrated to give the title compound (160 mg, 98%). LCMS RT=0.72 min, [M+H+(79Br)]=387.0, [M+H+(81Br)]=389.0.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate (40 ml)
  2. additiona mixture of aqueous (3:1:4, water, sodium bicarbonate solution and 20% w/w sodium thiosulfate solution, 40 ml)
  3. customThe organic phase was separated
  4. washwashed with water (3×30 ml), brine
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-92300415451b478a870dc525fda0b27a
Source dataset
uspto-grants-2015_10
Patent number
US09156853B2

Reaction notes

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