Triethylamine → HCID 58459069, compound

Temperature

50 °C

Charge 4,6-dichloro-2-methyl-pyrimidin-5-ylamine (307 g, 1.72 moles) into a 10 L flange flask mounted on an isomantle equipped with an overhead stirrer, reflux coil condenser, thermometer, and addition funnel. Then add isopropyl alcohol (3.45 L) to the flask and stir to give a clear pale yellow solution. Add triethylamine (456.7 mL, 3.28 mol) to the flask in one portion while stirring and warm to 50° C. Slowly add (R)-(−)-2-amino-1-propanol (194.30 g, 202.10 mL, 2.59 mol) from the addition funnel over 30 min. After the final addition heat the reaction mixture at reflux for 36 h. Allow the reaction mixture to cool. Add additional (R)-(−)-2-amino-1-propanol (64.77 g, 67.37 mL, 862.26 mmol, 0.5 eq) and triethylamine (174.51 g, 240.37 mL, 1.72 moles, 1.0 eq) to the reaction mixture and reflux for 18 h. Allow the reaction mixture to cool. Add additional (R)-(−)-2-amino-1-propanol (32.38 g, 33.68 mL, 431.13 mmol, 0.25 eq) and triethylamine (87.25 g, 120.18 mL, 862.26 mmol, 0.5 eq) to the reaction mixture and heat to reflux for 6 h. Allow to cool while stirring at ambient temperature for 48 h.

1. customan isomantle equipped with an overhead stirrer
2. temperaturereflux coil condenser
3. additionthermometer, and addition funnel
4. customto give a clear pale yellow solution
5. additionAfter the final addition
6. temperatureheat the reaction mixture
7. temperatureat reflux for 36 h
8. temperatureto cool
9. temperaturereflux for 18 h
10. temperatureto cool
11. temperatureheat
12. temperatureto reflux for 6 h
13. temperatureto cool

ORD record

ord-af3b3ed5995c465dbc5f370a44198caf

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08759360B2