4-BENZYLOXY-2-CHLOROPYRIMIDINE Chemical Properties

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 Information

Hazard Codes 

Xn

Risk Statements 

22-37/38-41

Safety Statements 

26-39

HS Code 

2933599590

4-BENZYLOXY-2-CHLOROPYRIMIDINE Usage And Synthesis

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

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