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4-HYDROXYPYRIMIDINE-5-CARBOXYLIC ACID (19). Ethyl 4-hydroxypyrimidine-5-carboxylate can be prepared following the procedure of M. Pesson et al., Eur. J. Med. Chem.-Chim. Ther. 1974, 9, 585. A solution of this ester (500 mg, 3 mmol) in THF (10 mL) and MeOH (5 mL) was treated with LiOH.H2O (373 mg, 8.9 mmol) and stirred overnight. The mixture was quenched with conc. HCl (1 mL) and extracted with EtOAc (2*20 mL). The combined organic extract was dried (MgSO4) and concentrated to give 260 mg of the title compound 19 as an orange solid, m.p. 220 C. (dec).
A mixture of ethyl 4-hydroxy-5-pyrimidinecarboxylic acid ester (1.5 g, 8.9 mmol), and potassium hydroxide (1.2 g, 21.4 mmol) in 10 mL of ethanol was stirred under nitrogen at 75 C. for approximately 20 hours. The mixture was diluted with 10 mL of diethyl ether, cooled to 0 C. and acidified to pH 1 with 12M hydrochloric acid to give a precipitate. The precipitate was isolated by filtration and dried in vacuo to give 4-hydroxy-5-pyrimidinecarboxylic acid (0.88 g, 6.3 mmol).
2
sodium salt of methyl 4-hydroxypyrimidine-5-carboxylate[ No CAS ]
[ 65754-04-3 ]
Yield
Reaction Conditions
Operation in experiment
3.55 g (78%)
In water;
Example 2b Process for the Preparation of 4-hydroxypyrimidine-5-carboxylic acid The moist sodium salt of methyl 4-hydroxypyrimidine-5-carboxylate obtained as in Example 2a) was taken up in water/tetrahydrofuran=1:1, and 1.0 eq of LiOH.H2 O was added. Following hydrolysis of the ester over 3.5 hours at 0 C. and 2 hours at room temperature, most of the tetrahydrofuran was evaporated and, at 0 C., a pH of 3 was adjusted using eq. HCl solution. After about 45 minutes at 0 C., the title product was filtered off. Drying gave the acid in a yield of 3.55 g (78%). 1 H NMR (DSOd6, 400 MHz)delta=8.6 (s, 1H); 8.7 (s, 1H); 11.8-14.7 (broad, 2H).
4-chloro-N,N-dimethyl-5-pyrimidinecarboxamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With thionyl chloride; triethylamine; In dichloromethane; N,N-dimethyl-formamide;
A mixture of <strong>[65754-04-3]4-hydroxy-5-pyrimidinecarboxylic acid</strong> (0.88 g, 6.3 mmol) in 5 drops of DMF and 6 mL of thionyl chloride was heated at reflux for 3 hours. The mixture was concentrated and the residue was dissolved in methylene chloride. A mixture of the residue, dimethylamine hydrochloride (0.62 g, 7.6 mmol) and triethylamine (4.5 mL, 31.5 mmol) in 50 mL of methylene chloride was stirred at 0 C. for 0.5 hours. The mixture was poured into water and aqueous sodium bicarbonate. The mixture was extracted with methylene chloride (2*30 mL) and the extract was washed with brine, dried (Na2 SO4) and concentrated by rotary evaporation to give 4-chloro-N,N-dimethyl-5-pyrimidinecarboxamide (0.66 g, 3.6 mmol) as an oil.
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