2-PYRIMIDINECARBOXYLIC ACID, METHYL ESTER Chemical Properties

Melting point:

104-105 °C

Boiling point:

251.3±23.0 °C(Predicted)

Density 

1.213±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

-1.42±0.13(Predicted)

color 

White to Almost white

InChI

InChI=1S/C6H6N2O2/c1-10-6(9)5-7-3-2-4-8-5/h2-4H,1H3

InChIKey

JOQJEWAXHQDQAG-UHFFFAOYSA-N

SMILES

C1(C(OC)=O)=NC=CC=N1

CAS DataBase Reference

34253-03-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Safety Statements 

24/25

HazardClass 

IRRITANT

HS Code 

29335990

2-PYRIMIDINECARBOXYLIC ACID, METHYL ESTER Usage And Synthesis

Uses

Methyl pyrimidine-2-carboxylate is a biochemical reagent that can be used as a biological material or organic compound for life science related research.

Synthesis

Step A: Preparation of methyl pyrimidine-2-carboxylate: a saturated HCl methanol solution was prepared by passing dry HCl gas into methanol (700 mL) for 30 min at 0 °C. To this solution was added pyrimidine-2-carbonitrile (21.585 g, 205.38 mmol) and the reaction was stirred at room temperature for 16 h. The reaction was then warmed up to 40-50 °C and continued to be stirred for 3 h. The reaction was then carried out under reduced pressure and concentrated. After completion of the reaction, the reaction mixture was concentrated under reduced pressure and the residue was dissolved in water. The pH of the aqueous phase was adjusted with solid sodium bicarbonate to 7.0. The aqueous phase was extracted with a 20% isopropanol/dichloromethane solvent mixture (3 times). The organic phases were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the white solid product methyl pyrimidine-2-carboxylate (23.0 g, 81% yield). The product was characterized by 1H NMR (400 MHz, CDCl3): δ 8.97-8.96 (d, J = 4.7 Hz, 2H), 7.53-7.50 (t, J = 4.7 Hz, 1H), 4.09 (s, 3H).

References

[1] Patent: US2010/63066, 2010, A1. Location in patent: Page/Page column 15
[2] Patent: US2007/49603, 2007, A1. Location in patent: Page/Page column 78; 53
[3] European Journal of Organic Chemistry, 2005, # 15, p. 3297 - 3303
[4] Patent: WO2008/42925, 2008, A1. Location in patent: Page/Page column 54-55
[5] Patent: WO2008/42925, 2008, A1. Location in patent: Page/Page column 54-55

2-PYRIMIDINECARBOXYLIC ACID, METHYL ESTER(34253-03-7)Related Product Information

• 2-PYRIMIDINECARBOXYLIC ACID, METHYL ESTER
• 5-Pyrimidinecarboxylic acid, methyl ester (6CI,7CI,8CI,9CI)
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• AURORA 19762
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