2-Pyrimidinemethanol, 4,6-dimethyl- (9CI)

2-Pyrimidinemethanol, 4,6-dimethyl- (9CI) Property

Melting point:

87-88 °C

Boiling point:

235.1±28.0 °C(Predicted)

Density 

1.130±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

13.75±0.10(Predicted)

Appearance

Light yellow to yellow Solid

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

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

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

2-Pyrimidinemethanol, 4,6-dimethyl- (9CI) Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of (4,6-dimethylpyrimidin-2-yl)methanol from methyl 4,6-dimethylpyrimidine-2-carboxylate: 4,6-dimethylpyrimidine-2-carboxylic acid methyl ester (400 mg, 2.40 mmol) was dissolved in ethanol (10 mL) under argon protection and cooled to 0 °C. Sodium borohydride (137 mg, 3.60 mmol) was then added and the reaction was slowly warmed to room temperature and stirred for 2 hours. The reaction progress was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the reaction was quenched with deionized water (15 mL) and extracted with dichloromethane (2 x 30 mL). The organic phases were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the crude product (4,6-dimethylpyrimidin-2-yl)methanol (285 mg, 86% yield) as a thick slurry. The crude product was used directly in the next reaction without further purification. The product was confirmed by 1H-NMR (CDCl3, 400 MHz): δ 6.91 (s, 1H), 4.71 (s, 2H), 2.50 (s, 6H). Liquid chromatography-mass spectrometry (LC-MS) analysis showed a purity of 96.66%, m/z 139.3 (M++1); chromatographic conditions: Eclipse XDB C-18 column (150×4.6 mm, 5 μm), mobile phase 0.05% trifluoroacetic acid/acetonitrile at a flow rate of 1.0 mL/min, and retention time of 4.03 min. TLC unfolding agent was 40% ethyl acetate/hexane (Rf=0.5).

References

[1] Patent: WO2013/142269, 2013, A1. Location in patent: Paragraph 0589; 0590; 0591