4-(4,6-Dichloropyrimidin-2-yl)morpholine Chemical Properties

Melting point:

139.0 to 143.0 °C

Boiling point:

392.9±52.0 °C(Predicted)

Density 

1.435±0.06 g/cm3(Predicted)

storage temp. 

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

solubility 

soluble in Toluene

form 

powder to crystal

pka

-1.07±0.50(Predicted)

color 

White to Almost white

InChIKey

OXCOCPRVQUEIOL-UHFFFAOYSA-N

Safety Information

HS Code 

29349990

4-(4,6-Dichloropyrimidin-2-yl)morpholine Usage And Synthesis

Synthesis

2,4,6-Trichloropyrimidine (5) (3.158 g, 17.22 mmol) was mixed with acetone (60 mL) and the mixture was cooled to 0 °C. Morpholine (7) (1.05 equiv, 1.576 g, 18.09 mmol) was slowly added at 0 °C, followed by stirring of the reaction mixture at 0 °C for 15 min, then warmed up to room temperature and continued stirring for 15 min. The progress of the reaction was monitored by thin layer chromatography (TLC, the unfolding agent was a hexane solution of 20% ethyl acetate). After completion of the reaction, the reaction mixture was concentrated by rotary evaporator and further dried under high vacuum. The crude product was purified by silica gel column chromatography using hexane solution of 20% ethyl acetate as eluent to afford the major regional isomer 2-morpholino-4,6-dichloropyrimidine (10) (3.183 g, 13.6 mmol, 79% yield). Elemental analysis (C8H9N3OCl2) Calculated values: C, 41.05; H, 3.88; measured values: C, 42.27; H, 4.06. 1H-NMR (300 MHz, CDCl3) δ 6.40 (s, 1H), 3.82-3.70 (m, 4H), 3.65 (m, 4H). High Resolution Mass Spectrometry (HRMS) [M]+ Calculated value: C8H9N3OCl2, 234.0201; Measured value: 234.0196. secondary regioisomer 4-(2,6-dichloropyrimidin-4-yl)morpholine (11) (0.806 g, 3.444 mmol, 20% yield). 1H-NMR (300 MHz, CDCl3) δ 6.56 (s, 1H), 3.85-3.60 (m, 8H). 13C-NMR (101MHz, CDCl3) δ 161.75, 160.55, 108.31, 66.59, 44.39. HRMS [M]+ calculated value: C8H9N3OCl2, 234.0201; measured value: 234.0196.

References

[1] Molecules, 2018, vol. 23, # 7, p. 1 - 13
[2] Patent: WO2015/49369, 2015, A1. Location in patent: Page/Page column 48; 49
[3] Patent: WO2016/75130, 2016, A1. Location in patent: Page/Page column 124-125
[4] Patent: WO2017/198347, 2017, A1. Location in patent: Page/Page column 88; 89
[5] Patent: WO2017/198346, 2017, A1. Location in patent: Page/Page column 77; 78

4-(4,6-Dichloropyrimidin-2-yl)morpholine(10397-13-4)Related Product Information

• Moroxydine
• Moroxydine hydrochloride
• 4,6-Dichloropyrimidine
• Dimethomorph
• 4-(2,6-dibromopyrimidin-4-yl)morpholine
• 4-(4,6-dibromopyrimidin-2-yl)morpholine
• 4-(2,6-DICHLOROPYRIMIDIN-4-YL)MORPHOLINE
• morpholine
• 2-Amino-4,6-dichloropyrimidine
• (4,6-DICHLORO-PYRIMIDIN-2-YL)-DIETHYLAMINE
• 4,6-DICHLORO-N,N-DIMETHYL-2-PYRIMIDINAMINE
• 4-(4,6-Dichloropyrimidin-2-yl)morpholine