Potassium Carbonate → HCID 117857076, compound

Temperature

90 °C

To a stirring suspension of 7-methyl-5-phenyl-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one (0.86 g, 3.82 mmol) in anhydrous DMF (30 ml) was added potassium carbonate (1.06 g, 7.64 mmol) and 1,1,1-trifluoro-2-iodoethane (0.564 ml, 5.73 mmol). The mixture was heated to 90° C. for 16 h. A further portion of potassium carbonate (1.06 g, 7.64 mmol) and 1,1,1-trifluoro-2-iodoethane (0.564 ml, 5.73 mmol) were added and the mixture heated to 90° C. for 24 h. The mixture was cooled and partitioned between brine/water (1:1, 300 ml) and ethyl acetate (75 ml). The aqueous portion was separated and extracted with ethyl acetate (3×75 ml). The combined organic fractions were washed with brine/water (1:1, 4×75 ml), dried (anhydrous sodium sulfate), filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (gradient 0-30% ethyl acetate in cyclohexane) to afford the title compound (719 mg, 61%). LCMS RT=1.25 min, M+H+=308.0.

1. temperaturethe mixture heated to 90° C. for 24 h
2. temperatureThe mixture was cooled
3. custompartitioned between brine/water (1:1, 300 ml) and ethyl acetate (75 ml)
4. customThe aqueous portion was separated
5. extractionextracted with ethyl acetate (3×75 ml)
6. washThe combined organic fractions were washed with brine/water (1:1, 4×75 ml)
7. dry with materialdried (anhydrous sodium sulfate)
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customThe residue was purified by silica gel chromatography (gradient 0-30% ethyl acetate in cyclohexane)

ORD record

ord-aa27cf610abc4c11a6991161f01cfa29

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09156853B2