Reaction #985308

Reaction equation

Cyclopropyl-4,4-diethoxy-but-2-yn-1-one

2-hexyl-isothiourea hydrobromide

triethylamine

→

colorless oil

Yield 84.5%

4-Cyclopropyl-6-diethoxymethyl-2-hexylsulfanyl-pyrimidine

Yield 84.5%

Solvents

THF

Conditions

Workup

1. 1
   Other(28° C.)
2. 2
   ExtractionThe product was extracted with AcOEt, sat. NH4Cl solution
3. 3
   Otherdried
4. 4
   Concentrationconcentrated
5. 5
   OtherThe residue was purified by silica gel chromatography in heptane/ethyl acetate 95:5

Procedure

Cyclopropyl-4,4-diethoxy-but-2-yn-1-one (2 g, 10 mmol) and 2-hexyl-isothiourea hydrobromide (2.7 g, 11.2 mmol) were dissolved under nitrogen in THF (20 mL). Then triethylamine (3.1 mL, 22.4 mmol) was added slowly. The reaction was slightly exothermic (28° C.). The suspension was stirred for 5 h at 20° C. The product was extracted with AcOEt, sat. NH4Cl solution, dried and concentrated. The residue was purified by silica gel chromatography in heptane/ethyl acetate 95:5. One obtained 2.86 g (83%) of a colorless oil. MS: m/z=339 (M+H).

Source