Triethylamine → HCID 66832471, compound

To a solution of 2-(4-trifluoromethyl-phenyl)-pyrimidine-4-carboxylic acid (435 mg, 1.60 mmol), Et3N (0.34 mL, 2.40 mmol) and THF (10 mL) was added isobutyl chloroformate (333 mg, 2.40 mmol). After 1 h, the resulting mixture was filtered through a fritted funnel and washed with THF (30 mL). The filtrate was concentrated to approximately 10 mL and MeOH (1 mL) was added followed by sodium borohydride (121 mg, 3.20 mmol). After 12 h, the mixture was partitioned between saturated aqueous NaHCO3 (30 mL) and ethyl acetate (30 mL). The aqueous layer was extracted with ethyl acetate (2×30 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated. The residue was purified directly by FCC to afford a white solid (120 mg, 27%). MS (ESI): mass calcd. for C12H9F3N2O; 254.0 m/z found, 255.1 [M+H]+. 1H NMR (500 MHz, CDCl3) δ 8.80 (d, J=5.1, 1H), 8.57 (d, J=8.1, 2H), 7.75 (d, J=8.2, 2H), 7.30 (d, J=5.1, 1H), 4.85 (s, 2H).

1. filtrationthe resulting mixture was filtered through a fritted funnel
2. washwashed with THF (30 mL)
3. concentrationThe filtrate was concentrated to approximately 10 mL and MeOH (1 mL)
4. additionwas added
5. waitAfter 12 h
6. customthe mixture was partitioned between saturated aqueous NaHCO3 (30 mL) and ethyl acetate (30 mL)
7. extractionThe aqueous layer was extracted with ethyl acetate (2×30 mL)
8. dry with materialThe combined organic layers were dried (MgSO4)
9. filtrationfiltered
10. concentrationconcentrated
11. customThe residue was purified directly by FCC

ORD record

ord-1d1e3f7a74a841ab8fdc810996df7440

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08614201B2