Ethanone,1-(4-pyrimidinyl)-

Ethanone,1-(4-pyrimidinyl)- Property

Melting point:

67 °C

Boiling point:

70 °C(Press: 3 Torr)

Density 

1.136±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

-0.39±0.10(Predicted)

Appearance

White to yellow Solid

InChI

InChI=1S/C6H6N2O/c1-5(9)6-2-3-7-4-8-6/h2-4H,1H3

InChIKey

UZKADDSUUBRMKO-UHFFFAOYSA-N

SMILES

C(=O)(C1C=CN=CN=1)C

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

Ethanone,1-(4-pyrimidinyl)- Chemical Properties,Usage,Production

Synthesis

Example 1: General procedure for the synthesis of 4-pyrimidine acetophenone from pyrimidine and acetaldehyde 1. dissolve pyrimidine (2.5 g, 31.2 mmol) and acetaldehyde (10.8 mL, 192 mmol) in dichloromethane (190 mL) at 0 °C with stirring and slowly add 3.4 M sulfuric acid (15.6 mL). 2. The reaction solution was cooled to -5°C and the following two solutions were added dropwise through two different dropping funnels simultaneously over a period of about 30 minutes: - 80% tert-butyl hydroperoxide in tert-butyl oxide/water solution (23.4 mL) - A solution of ferrous sulfate heptahydrate (52.2 g) dissolved in 100 mL of water. 3. After the dropwise addition was completed, the reaction mixture was continued to be stirred at 0 °C for 2.5 hours. 4. After completion of the reaction, the phases were separated and the aqueous phase was extracted with dichloromethane (2 x 150 mL). 5. The organic phases were combined and washed sequentially with 10% aqueous sodium iodide, 10% aqueous Na2S2O5 and brine, then dried with anhydrous Na2SO4. 6. The dried organic phase was concentrated and the yellow solid obtained was absorbed with petroleum ether and filtered. 7. After drying, 4-pyrimidine ethanone was obtained as a brown solid (0.87 g, 23% yield).

References

[1] Drug Metabolism and Disposition, 2011, vol. 39, # 12, p. 2355 - 2360
[2] Journal of Medicinal Chemistry, 1992, vol. 35, # 17, p. 3288 - 3296
[3] Patent: WO2005/14572, 2005, A1. Location in patent: Page/Page column 24