4-BENZYLOXY-2-CHLOROPYRIMIDINE

4-BENZYLOXY-2-CHLOROPYRIMIDINE Property

Boiling point:

387.0±17.0 °C(Predicted)

Density 

1.278±0.06 g/cm3(Predicted)

storage temp. 

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

pka

0.06±0.20(Predicted)

Appearance

White to light yellow Solid

InChI

InChI=1S/C11H9ClN2O/c12-11-13-7-6-10(14-11)15-8-9-4-2-1-3-5-9/h1-7H,8H2

InChIKey

SNCGVIVLUWJDQN-UHFFFAOYSA-N

SMILES

C1(Cl)=NC=CC(OCC2=CC=CC=C2)=N1

Safety

Hazard Codes 

Xn

Risk Statements 

22-37/38-41

Safety Statements 

26-39

HS Code 

2933599590

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.

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.

P405Store locked up.

4-BENZYLOXY-2-CHLOROPYRIMIDINE Chemical Properties,Usage,Production

Synthesis

Step 1. 2.26 g (20.1 mmol, 1 eq.) of potassium tert-butanolate and 4.3 g (40.2 mmol, 2 eq.) of benzyl alcohol were dissolved in 10 mL of THF under dry conditions, and the resulting mixture was heated under reflux conditions for 30 min. Subsequently, the reaction mixture was cooled to 0 °C and 3 g (20.1 mmol, 1 eq.) of 2,4-dichloropyrimidine solution dissolved in 15 mL of N,N-dimethylformamide was added drop-wise under strictly controlled conditions below 0 °C. After the dropwise addition, the reaction was continued to be stirred at 0 °C for 1 h, and then warmed up to room temperature naturally. The reaction mixture was slowly poured into 100 mL of ice water and a white solid 4-benzyloxy-2-chloropyrimidine was precipitated, which was collected by filtration to give 3.3 g of product in 75% yield. The structure of the product was confirmed by LC-MS (LC-MS (m/z) = 222.0 [M + H]+).

References

[1] Organic Letters, 2017, vol. 19, # 7, p. 1854 - 1857
[2] Chemistry - A European Journal, 2017, vol. 23, # 58, p. 14563 - 14575
[3] Patent: WO2011/19405, 2011, A1. Location in patent: Page/Page column 107
[4] Patent: US2011/195980, 2011, A1. Location in patent: Page/Page column 28
[5] Patent: EP1564212, 2005, A1. Location in patent: Page 13