Methyl 2,4-dichloropyrimidine-6-carboxylate → HCID 86633637, compound

Temperature

80 °C

Pd(dppf)Cl2 (0.214 g, 0.02 mmol) was added to a mixture of methyl 2,4-dichloropyrimidine-6-carboxylate (2.07 g, 10 mmol) and 4-(trifluoromethyl)phenyl-boronic acid (1.90 g, 10 mmol) in DME (100 mL) and sat. aq. NaHCO3 (20 mL), and the mixture was stirred in an atmosphere of argon at 80° C. for 3 h. The reaction mixture was cooled to 20° C. and added to ice water (100 mL). The mixture was extracted with ethyl acetate (2×100 mL) and the organic phase was extracted with saturated sodium carbonate solution (50 mL). The combined aqueous layers were acidified by the addition of 25% HCl (100 mL) and subsequently extracted with ethyl acetate (2×100 mL). The organic phase was washed with brine, dried over sodium sulfate, and the solvents were removed under reduced pressure. The residual solid was recrystallized from ethyl acetate/heptane to give the title compound (1.82 g, 60%) as light red solid. MS ISN (m/e): 301.2 [(M−H)−]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=8.51 (s, 1H), 8.33 and 7.84 (2 d, 2×2H).

1. temperatureThe reaction mixture was cooled to 20° C.
2. extractionThe mixture was extracted with ethyl acetate (2×100 mL)
3. extractionthe organic phase was extracted with saturated sodium carbonate solution (50 mL)
4. additionThe combined aqueous layers were acidified by the addition of 25% HCl (100 mL)
5. extractionsubsequently extracted with ethyl acetate (2×100 mL)
6. washThe organic phase was washed with brine
7. dry with materialdried over sodium sulfate
8. customthe solvents were removed under reduced pressure
9. customThe residual solid was recrystallized from ethyl acetate/heptane

ORD record

ord-52b92586c01a4b0e8e22f3534ebc7305

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08962834B2