Hydrochloric Acid → HCID 19980404, compound

19.6 g (86.3 mmol) of 2-phenylamino-4-hydroxy-6-cyclopropyl-pyrimidine are added to 50 ml (0.55 mol) of phosphorus oxychloride at 75° C. in the course of one hour, while stirring, and the mixture is then refluxed for one hour. When the evolution of hydrogen chloride has ended, the reaction mixture is cooled to room temperature and poured into 200 ml of water, while stirring vigorously, the temperature being kept at about 50° C. by addition of ice. The approximately 400 ml of the pale brown suspension is brought to pH 7 by slow dropwise addition of 220 ml of 30% aqueous sodium hydroxide solution and is extracted three times with 150 ml of ethyl acetate each time. The combined extracts are washed twice with 100 ml of water each time, dried over sodium sulfate and filtered and the solvent is evaporated. The 20.7 of pale brown powder are treated with 400 ml of diethyl ether and the undissolved material is filtered off. After evaporation of the diethyl ether, the residue is recrystallized from diisopropyl ether. The yellowish crystals melt at 127°-128° C. Yield 17.7 g (72.1 mmol; 83.5% of theory).

1. temperaturethe mixture is then refluxed for one hour
2. stirringwhile stirring vigorously
3. additionthe temperature being kept at about 50° C. by addition of ice
4. extractionis extracted three times with 150 ml of ethyl acetate each time
5. washThe combined extracts are washed twice with 100 ml of water each time
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. customthe solvent is evaporated
9. additionThe 20.7 of pale brown powder are treated with 400 ml of diethyl ether
10. filtrationthe undissolved material is filtered off
11. customAfter evaporation of the diethyl ether
12. customthe residue is recrystallized from diisopropyl ether
13. custommelt at 127°-128° C

ORD record

ord-d6d90100da08478dbe2210d7acfbcddd

Source dataset

uspto-grants-1991_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05075316