Trifluoroacetic anhydride → 5-Amino-2-phenyl-pyrimidine-4-carboxylic acid methyl ester

To 4.0 g (0.0186 mole) of 5-amino-2-phenyl-pyrimidine-4-carboxylic acid in an ice bath was slowly added 48 mL of trifluoroacetic anhydride and the mixture was heated to 50° C. for 5 h. The reaction mixture was filtered, washed with a little trifluoroacetic anhydride and dried. To a suspension of the resulting product in 50 mL of methanol, was added 0.1 mL of 0.5M sodium methoxide in methanol. The mixture was refluxed for 15 minutes, cooled to room temperature, and HCl gas was bubbled in for one hour. After cooling and filtering, the solid was treated with 200 ml of 1N NaOH and 200 ml ether. The organic layer was dried over magnesium sulfate, filtered, evaporated to yield 2.43 g of 5-amino-2-phenyl-pyrimidine-4-carboxylic acid methyl ester, as a yellow solid.

1. filtrationThe reaction mixture was filtered
2. washwashed with a little trifluoroacetic anhydride
3. customdried
4. additionTo a suspension of the resulting product in 50 mL of methanol
5. additionwas added 0.1 mL of 0.5M sodium methoxide in methanol
6. temperatureThe mixture was refluxed for 15 minutes
7. customHCl gas was bubbled in for one hour
8. temperatureAfter cooling
9. filtrationfiltering
10. additionthe solid was treated with 200 ml of 1N NaOH and 200 ml ether
11. dry with materialThe organic layer was dried over magnesium sulfate
12. filtrationfiltered
13. customevaporated

ORD record

ord-38166571974245f291434faacf42a546

Source dataset

uspto-grants-2003_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06569860B2