Diisopropylethylamine → 6-(Trifluoromethyl)-N-{[2-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]methyl}-4-pyrimidinamine

1-[2-(Trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]methanamine (Intermediate 5, 130 mg, 0.604 mmol), 4-chloro-6-(trifluoromethyl)pyrimidine (165 mg, 0.906 mmol) and DIPEA (0.211 mL, 1.208 mmol) in N-methyl-2-pyrrolidone (2 mL) were stirred at 150° C. for 1 hour in the microwave. The reaction mixture was diluted with ethyl acetate (25 mL) and washed with water (10 mL), brine (10 mL), water (10 mL) and brine (10 mL). The organic layer was dried (sodium sulfate), filtered and concentrated under reduced pressure to give a brown oil. This oil was dissolved in a mixture of acetonitrile and DMSO (1:1) (2.7 mL) and purified by MDAP (3 injections). Fractions containing the suspected product were combined and concentrated under reduced pressure to give the title compound as a pale brown solid (72 mg);

1. washwashed with water (10 mL), brine (10 mL), water (10 mL) and brine (10 mL)
2. dry with materialThe organic layer was dried (sodium sulfate)
3. filtrationfiltered
4. concentrationconcentrated under reduced pressure
5. customto give a brown oil
6. custompurified by MDAP (3 injections)
7. additionFractions containing the suspected product
8. concentrationconcentrated under reduced pressure

ORD record

ord-731242e8fd914d4cb5d14be2b8b1104b

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08796283B2