Hydrochloric Acid → HCID 178512299, compound

To an ice-cooled solution of 2-chloro-4-pyrimidinecarbonitrile (23 g, 0.16 mol) in toluene (500 mL) was added methanol (7.5 mL, 0.18 mol), followed by treatment with gaseous hydrogen chloride for 2 h. The HCl-saturated solution was sealed and stirred overnight at room temperature, and then the white solid was collected by filtration and washed with diethyl ether (200 mL) and ethyl acetate (200 mL). The solid was then dissolved in methanol (400 mL) and treated with ammonia solution (100 mL, 7 M in MeOH) at room temperature. After stirring 4 h, the solution was concentrated in vacuo and the residue washed with ethyl acetate (200 mL). The resulting crude solid was dissolved in a mixture of water (150 mL) and isopropanol (50 mL), and to this solution was added cyanamide (8.5 g, 0.2 mol), and sodium bicarbonate (9 g, 0.1 mol). The mixture was stirred at room temperature for 5 h, cooled to 0° C. and stirred for an additional 5 h. The resulting grey mixture was filtered, rinsed with water, and dried in vacuo for 24 h to give 13 g of the title compound as a white solid.

1. filtrationthe white solid was collected by filtration
2. washwashed with diethyl ether (200 mL) and ethyl acetate (200 mL)
3. dissolutionThe solid was then dissolved in methanol (400 mL)
4. additiontreated with ammonia solution (100 mL, 7 M in MeOH) at room temperature
5. stirringAfter stirring 4 h
6. concentrationthe solution was concentrated in vacuo
7. washthe residue washed with ethyl acetate (200 mL)
8. dissolutionThe resulting crude solid was dissolved in a mixture of water (150 mL) and isopropanol (50 mL)
9. stirringThe mixture was stirred at room temperature for 5 h
10. temperaturecooled to 0° C.
11. stirringstirred for an additional 5 h
12. filtrationThe resulting grey mixture was filtered
13. washrinsed with water
14. customdried in vacuo for 24 h

ORD record

ord-aacb5b97529c43a28cd74dff003c333c

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08026359B2