5-CYANOPYRIMIDINE Chemical Properties

Melting point:

83.5-84 °C(Solv: ethanol (64-17-5))

Boiling point:

237.6±13.0 °C(Predicted)

Density 

1.22±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform, Dichloromethane, Ethyl Acetate, Methanol

form 

Solid

pka

0.78±0.10(Predicted)

color 

Pale Yellow

Safety Information

Risk Statements 

36

Safety Statements 

26-24/25

Hazard Note 

Harmful

HS Code 

29335990

5-CYANOPYRIMIDINE Usage And Synthesis

Chemical Properties

Pale Yellow Solid

Uses

5-Cyanopyrimidine (cas# 40805-79-6) is a compound useful in organic synthesis.

Synthesis

General procedure for the synthesis of 5-cyanopyrimidine from pyrimidine-5-carboxamide: To a suspension of anhydrous dichloromethane (15 mL) containing pyrimidine-5-carboxamide (262 mg, 2.12 mmol) and triethylamine (481 mg, 4.24 mmol) was added slowly and dropwise a solution of trifluoroacetic anhydride (0.36 mL, dissolved in 4 mL of dichloromethane) at 0 °C. The reaction mixture was stirred at 0°C to room temperature for 2 hours. After completion of the reaction, it was quenched with water (2 mL) and the organic layer was washed sequentially with 1N NaOH solution (5 mL) and brine (2 x 5 mL). The organic phase was dried with anhydrous magnesium sulfate and subsequently concentrated under reduced pressure at less than 30 °C to afford the light yellow solid product 5-cyanopyrimidine (174 mg, 78% yield). The product was characterized by 1H NMR (400 MHz, DMSO): δ 9.44 (s, 1H), 9.31 (s, 2H).

References

[1] Patent: WO2012/129564, 2012, A2. Location in patent: Page/Page column 79
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 10, p. 3783 - 3805
[3] Journal of Organic Chemistry, 2015, vol. 80, # 5, p. 2676 - 2699
[4] Patent: WO2009/148452, 2009, A1. Location in patent: Page/Page column 71

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