Pyrimidine-2-carboxylic acid Chemical Properties

Melting point:

182-185°C

Boiling point:

362.6±25.0 °C(Predicted)

Density 

1.403±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Soluble in ethanol, Dimethyl sulfoxide (DMSO), Dimethylformamide (DMF), and solution of Phosphate Buffered Saline (PBS).

form 

powder to crystal

pka

3.08±0.10(Predicted)

color 

White to Almost white

λmax

246nm(H2O (pH 7))(lit.)

InChIKey

ZFCHNZDUMIOWFV-UHFFFAOYSA-N

CAS DataBase Reference

31519-62-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29335990

Pyrimidine-2-carboxylic acid Usage And Synthesis

Description

2-carboxy-Pyrimidine is a synthetic intermediate useful for pharmaceutical synthesis.

Chemical Properties

White to off-white solid

Uses

2-carboxy-Pyrimidine is a synthetic intermediate.

Synthesis

Synthesis of pyrimidine-2-carboxylic acid (11): pyrimidine-2-carbonitrile (10) (201 mg, 1.914 mmol) was dissolved in water (5 mL) under stirring conditions, followed by addition of KOH (214.3 mg, 3.83 mmol). The reaction mixture was heated to reflux for 3 hours. The progress of the reaction was monitored by thin layer chromatography (TLC) and after confirming the complete consumption of raw materials, the reaction mixture was slowly cooled to room temperature. The reaction mixture was neutralized with 2N HCl solution and subsequently the aqueous phase was removed by rotary evaporation to give the crude product. The crude product was extracted with ethyl acetate (EtOAc), the organic phases were combined and filtered through a diatomaceous earth pad. The filtrate was concentrated under reduced pressure to afford pyrimidine-2-carboxylic acid (11) (84 mg, 35.4% yield), which could be used in subsequent reactions without further purification.TLC conditions: 80% EtOAc/hexane (Rf: 0.05).1H NMR (400 MHz, CD3OD-d4): δ 8.83 (br s, 2H), 7.47 (t, J = 4.8 Hz, 1H).

References

[1] Dalton Transactions, 2011, vol. 40, # 20, p. 5476 - 5482
[2] Journal of Organic Chemistry, 2015, vol. 80, # 5, p. 2676 - 2699
[3] Chemical Communications, 2016, vol. 52, # 54, p. 8459 - 8462
[4] Patent: WO2013/13238, 2013, A2. Location in patent: Page/Page column 49
[5] Patent: KR2015/128789, 2015, A. Location in patent: Paragraph 0818; 0820; 0821

Pyrimidine-2-carboxylic acid(31519-62-7)Related Product Information

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• Ethyl 2-(Chlorosulfonyl)acetate
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• Pyrimidine
• Cytosine
• Fluorocytosine
• 9-Fluorenylmethyl chloroformate
• Octyl gallate
• 2-Pyrimidinecarboxaldehyde
• 2-Pyrimidinecarboxamide (6CI,7CI,9CI)
• Pyrimidine-5-boronic acid pinacol ester
• 5-Pyrimidinecarboxylic acid
• PYRIMIDINE-4-CARBOXALDEHYDE
• Pyrimidine-5-carboxaldehyde
• Pyrrole-2-carboxaldehyde
• PYRROLE-2-CARBONITRILE
• Pyrrole-2-carboxylic acid