Water → HCID 57566546, compound

Temperature

100 °C

To a solution of 2-(3,5-difluoro-2-nitro-phenyl)-pyrimidine (1.5 g, 6.32 mmoles) in dioxane (10 mL) was added tBuNH2 (6.6 mL, 63.24 mmoles) at room temperature. The mixture was heated to 100° C. in a sealed tube for 10 hours. The mixture was then cooled to room temperature, poured into water, and the solids stirred for 1 hour. The mixture was filtered, solids washed with water until filtrate was clear. The crude product was then diluted in MeOH, 6N HCl added, and the resulting mixture heated at reflux for 3 hours. The reaction was cooled to room temperature and poured into ice. The resulting heterogeneous mixture was warmed to room temperature, filtered, solids washed with water until filtrate ran clear, and dried in vacuo to afford the title compound (1.33 g, 90%) as an orange powder. 1H NMR (dmso-d6, 500 MHz): 8.87 (d, 2H); 7.52 (dd, 1H); 7.08 (dd, 1H); 6.86 (dd, 1H); 6.60 (s, 2H).

1. temperatureThe mixture was then cooled to room temperature
2. filtrationThe mixture was filtered
3. washsolids washed with water until filtrate
4. additionThe crude product was then diluted in MeOH
5. addition6N HCl added
6. temperaturethe resulting mixture heated
7. temperatureat reflux for 3 hours
8. temperatureThe reaction was cooled to room temperature
9. additionpoured into ice
10. temperatureThe resulting heterogeneous mixture was warmed to room temperature
11. filtrationfiltered
12. washsolids washed with water until filtrate
13. customdried in vacuo

ORD record

ord-e4e2a793a522412d95eaabdce39a95f9

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08394803B2