Acetic Acid → HCID 59140961, compound

Temperature

115 °C

A 250 ml 3-neck flask was equipped with an overhead stirrer, reflux condenser, and a thermocouple. The flask was charged with 2-amino-4-methyl-5-cyanopyrimidine (8.00 g, 59.64 mmol) and an anhydrous NaOAc ((0.035 g, 0.43 mmol) in a mixture of HOAc (16.00 g, 266.43 mmol) and Ac2O (16.00 g, 156.72 mmol). The resultant suspension was stirred and heated to 115° C. to yield a brown suspension, which was stirred at 115° C. for 2 h during which time all starting material dissolved to yield a solution. The resultant mixture was heated at 115° C. for 6.5 hours and then cooled to room temperature to afford a suspension. Toluene (69.70 g) was added to the suspension, and the resultant mixture was then heated to about 108-114° C. to distill about 70 ml of solvent atmospherically (solution was effected at 70° C.). The resultant solution was cooled, fresh toluene (69.70 g) was added, and about 90 ml of solvent was distilled atmospherically at about 110-115° C. The resultant solution was cooled to 90° C., whereupon the mixture began to solidify. Toluene (8.7 g) and heptane (61.2 g) were added and the resultant suspension was stirred and gradually cooled to room temperature. After stirring at room temperature for 1 h, the suspension was filtered and the solid was washed twice with heptane (27.2 g portions) and then dried in a vacuum oven at 70° C. overnight. The title compound —N-(4-Methyl-5-cyano-2-pyrimidinyl)-acetamide—was isolated as a solid.

1. customA 250 ml 3-neck flask was equipped with an overhead stirrer
2. temperaturereflux condenser
3. customto yield a brown suspension, which
4. dissolutiondissolved
5. customto yield a solution
6. temperaturecooled to room temperature
7. customto afford a suspension
8. distillationto distill about 70 ml of solvent atmospherically (solution was effected at 70° C.)
9. temperatureThe resultant solution was cooled
10. additionfresh toluene (69.70 g) was added
11. distillationabout 90 ml of solvent was distilled atmospherically at about 110-115° C
12. temperatureThe resultant solution was cooled to 90° C., whereupon the mixture
13. additionToluene (8.7 g) and heptane (61.2 g) were added
14. stirringthe resultant suspension was stirred
15. temperaturegradually cooled to room temperature
16. stirringAfter stirring at room temperature for 1 h
17. filtrationthe suspension was filtered
18. washthe solid was washed twice with heptane (27.2 g portions)
19. customdried in a vacuum oven at 70° C. overnight

ORD record

ord-35e47598631546f7a954512101ede4d1

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09006432B2