Sodium Hydroxide → HCID 72192370, compound

Temperature

40 °C

A mixture of ethyl 6-oxo-2-((4-(piperidin-1-yl)phenyl)amino)-1,6-dihydropyrimidine-5-carboxylate (100 mg, 0.298 mmol), sodium hydroxide (1M, aq), and methanol was stirred at 70° C. for 2 hours and for 40° C. overnight. The reaction mixture was filtered to remove the solid precipitate to verify product. Recombined the filtrate and precipitate to concentrate by adding 3 mL dioxane and heated to 103° C. for 4 hours with an additional 1 mL of NaOH added. The reaction mixture was then heated at 40° C. overnight. After the overnight heating, the reaction mixture was cooled and the solvent removed. The reaction mixture was diluted with water, and the pH was adjusted to about 3.0. The reaction mixture was filtered to obtain the end product. 1H-NMR confirmed the product (55 mg, 60% yield).

1. filtrationThe reaction mixture was filtered
2. customto remove the solid precipitate
3. concentrationto concentrate
4. additionby adding 3 mL dioxane
5. temperatureheated to 103° C. for 4 hours with an additional 1 mL of NaOH
6. additionadded
7. temperatureThe reaction mixture was then heated at 40° C. overnight
8. temperatureAfter the overnight heating
9. temperaturethe reaction mixture was cooled
10. customthe solvent removed
11. additionThe reaction mixture was diluted with water
12. filtrationThe reaction mixture was filtered
13. customto obtain the end product

ORD record

ord-292aa1dc283e49e6a92782ec8bf672db

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09309232B2