Ammonium Chloride → Pyrimidine-4-carboximidamide

Into a 250-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of Na (0.11 g) in methanol (100 mL). The mixture was stirred for 10 min. This was followed by the addition of pyrimidine-4-carbonitrile (10 g, 95.15 mmol, 1.00 equiv). The solution was stirred for 2 h at room temperature. To this was added NH4Cl (11 g, 205.65 mmol, 2.16 equiv). The resulting solution was stirred for 4 h at 25° C. The resulting mixture was concentrated under vacuum. The residue was dissolved in 100 mL of ethanol. The mixture was stirred for 10 min under reflux. The solids were filtered out. The filtrate was concentrated under vacuum. The solids were collected by filtration. This resulted in 5 g (33%) of pyrimidine-4-carboximidamide hydrochloride as a white solid. MS (ESI) m/z 123 ([M+H]+).

1. customInto a 250-mL 3-necked round-bottom flask purged
2. temperaturemaintained with an inert atmosphere of nitrogen
3. stirringThe solution was stirred for 2 h at room temperature
4. stirringThe resulting solution was stirred for 4 h at 25° C
5. concentrationThe resulting mixture was concentrated under vacuum
6. dissolutionThe residue was dissolved in 100 mL of ethanol
7. stirringThe mixture was stirred for 10 min
8. temperatureunder reflux
9. filtrationThe solids were filtered out
10. concentrationThe filtrate was concentrated under vacuum
11. filtrationThe solids were collected by filtration
12. customThis resulted in 5 g (33%) of pyrimidine-4-carboximidamide hydrochloride as a white solid

ORD record

ord-1d144cb37f1c4591932d2bcb6da6b874

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09193707B2