Ethyl butyrate → 5-Ethyl-2-thiouracil

To a suspension of potassium tert-butoxide (12.08 g, 108 mmol) in THF (40 mL) was added a solution of ethyl butyrate (5.69 mL, 43.0 mmol) and ethyl formate (6.93 mL, 86 mmol) in diethyl ether (40.0 mL) dropwise under nitrogen. The mixture was stirred at room temperature for 3 h. After removing the solvent, the residue oil was dissolved in isopropanol (350 mL), and thiourea (6.55 g, 86 mmol) was added. The mixture was stirred at reflux overnight, and then concentrated in vacuo to get a solid. The solid was dissolved in water, adjusted pH to 4 with AcOH, and extracted by DCM. The organic layer was dried over Na2SO4, filtered and concentrated to afford the title compound (5.5 g, 82% yield) as a pink solid.

1. customAfter removing the solvent
2. dissolutionthe residue oil was dissolved in isopropanol (350 mL)
3. stirringThe mixture was stirred
4. temperatureat reflux overnight
5. concentrationconcentrated in vacuo
6. customto get a solid
7. extractionextracted by DCM
8. dry with materialThe organic layer was dried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated

ORD record

ord-267e12404e0a49179f013a737b5f339a

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09174968B2