Methyl formate → Methyl 3-(4-oxo-2-thioxo-1,2,3,4-tetrahydro-5-pyrimidinyl)propanoate

To a suspension of potassium tert-butoxide (7.29 g, 64.9 mmol) in t-butylmethyl ether (100 mL) was added a solution of dimethyl pentanedioate (5.2 g, 32.5 mmol) and methyl formate (1.950 g, 32.5 mmol) in t-butylmethyl ether (50 mL). The mixture was stirred overnight and concentrated to dryness afford the yellow oil. The oil was dissolved in methanol (80 mL), to which thiourea (2.72 g, 35.7 mmol) was added. The mixture was heated to reflux overnight. The result mixture was concentrated and dissolved in water, adjust pH to 3 with AcOH. The solution was extracted with DCM three times. The combined organic layers were dried over Na2SO4, filtered and concentrated to afford the title compound (2.1 g, 9.80 mmol, 30.2% yield).

1. concentrationconcentrated to dryness
2. customafford the yellow oil
3. additionwas added
4. temperatureThe mixture was heated
5. temperatureto reflux overnight
6. concentrationThe result mixture was concentrated
7. dissolutiondissolved in water
8. extractionThe solution was extracted with DCM three times
9. dry with materialThe combined organic layers were dried over Na2SO4
10. filtrationfiltered
11. concentrationconcentrated

ORD record

ord-31d966fc43d943ff85f9fced238701b1

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09174968B2