Potassium Carbonate → HCID 89810825, compound

HRID 1750329Notes

Reaction equation

HRID 1750329 reaction equation
[I:1][C:2]1[C:10]2[C:9](=[O:11])[NH:8][CH:7]=[N:6][C:5]=2[N:4]([CH3:12])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[F:19][C:20]([F:24])([F:23])[CH2:21]I>CN(C=O)C>[I:1][C:2]1[C:10]2[C:9](=[O:11])[N:8]([CH2:21][C:20]([F:24])([F:23])[F:19])[CH:7]=[N:6][C:5]=2[N:4]([CH3:12])[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 677091,1,1-Trifluoro-2-iodoethaneHCID 1365990221459230-34-2

Product 1

HCID 89810825HCID 89810825, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred suspension of 5-iodo-7-methyl-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one (13.7 g, 49.8 mmol) in anhydrous DMF (137 ml) was added potassium carbonate (13.8 g, 100 mmol) and 1,1,1-trifluoro-2-iodoethane (7.36 ml, 74.7 mmol). The resulting mixture was heated at 90° C. for 24 h. The reaction mixture was partitioned between brine/water (1:1, 1.41) and ethyl acetate (350 ml). The organic phase was separated and the aqueous phase was extracted with ethyl acetate (3×350 ml). The combined organic phase was washed with brine/water (1:1, 4×350 ml), dried and concentrated. The residue was purified by flash chromatography (0-45% ethyl acetate/cyclohexane) to give the title compound (13.7 g, 77%). LCMS RT=1.05 min, M+H+=358.0.

Workup

  1. customThe reaction mixture was partitioned between brine/water (1:1, 1.41) and ethyl acetate (350 ml)
  2. customThe organic phase was separated
  3. extractionthe aqueous phase was extracted with ethyl acetate (3×350 ml)
  4. washThe combined organic phase was washed with brine/water (1:1, 4×350 ml)
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (0-45% ethyl acetate/cyclohexane)

Sources & evidence

ORD record
ord-0cd8206c8f03486fa776c119a41c2fe8
Source dataset
uspto-grants-2015_10
Patent number
US09156853B2

Reaction notes

Loading…