4-Hydroxy-6-(trifluoromethyl)pyrimidine

White powder

To a three-necked flask was added ethyl trifluoroacetoacetate (0.16 mL, 1.0 eq.), DBU (0.19 mL, 1.2 eq.), Add absolute ethanol (10 mL) to dissolve.A solution of formamidine hydrochloride in ethanol (0.09 g of formamidine hydrochloride in 2 mL of ethanol, The amount of formamidine hydrochloride1.05 eq.).Dropping the temperature to 70-80 ° C for 3 to 5 hours.TLC monitoring, The reaction was complete.The solvent was distilled off under reduced pressure, Diluted with water (20 mL)With 1mol / L hydrochloric acid adjusted pH = 6 ~ 7, Extraction with ethyl acetate (3 x 8 mL)The organic phase was combined with anhydrous sulfuric acidSodium drying, filtration, vacuum distillation of the solvent was light yellow solid, add petroleum ether (5mL) shock, filter, filter cake washed with petroleum ether, The oven was dried at 55 ° C for 2 hours to give a pale yellow flake solid in 96percent yield.An amount of 6-trifluoromethyl-pyrimidine-4-ol (1) (0.01 mol) and ethyl chloroacetate (0.01 mol) was dissolved in 20 mL of acetone by adding K2CO3 (0.01 mol). The reaction mixture was refluxed for 15 h on a water bath with constant stirring. After completion of the reaction (monitored by the TLC), the mixture was cooled, poured onto a mixture of ice and water. The formed precipitate was filtered, washed with distilled water. The resulting solid was recrystallized from ethanol to give pure (6-trifluoromethyl-pyrimidin-4-yloxy)acetic acid ethyl ester (2). Yield: 72 %, m.p.: 115-117 C, IR (KBr, numax, cm-1): 3037 (C-H, pyrimidine), 2968 (C-H, CH3), 1742 (C=O), 1590 (C=C, pyrimidine), 1476 (C=N), 1221 (C-O). 1H NMR (300 MHz, DMSO-d6) delta ppm: 7.78 (s, 1H, CH, pyrimidine), 7.55 (s, 1H, CH, pyrimidine), 4.14 (q, 2H, J = 5.4 Hz, CH2), 3.46 (s, 2H, CH2CO), 1.26 (t, 3H, J = 5.4 Hz, CH3). 13C NMR (100 MHz, DMSO-d6) delta ppm: delta 171.4, 136.5, 131.7, 122.8, 121.7, 73.1, 68.8, 59.5, 13.6. MS: m/z 250 (M+). Anal. calcd.(%) for C9H9N2O3F3: C-43.21, H-3.63, F-22.78, N-11.20, O-19.19. Found (%): C-42.89, H-3.62, F-22.39, N-11.09, O-18.98.

6-(Trifluoromethyl)-4-pyrimidinol is used as building block in chemical synthesis. Attributes Development Product Contact

Molecular Weight:164.09
XLogP3:0.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Exact Mass:164.01974721
Monoisotopic Mass:164.01974721
Topological Polar Surface Area:41.5
Heavy Atom Count:11
Complexity:241
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes