Reaction #985317

Reaction equation

1-(2-Hexylsulfanyl-6-methyl-pyrimidin-4-yl)-ethanone

morpholine

sodium cyanoborohydride

→

yellow oil

Yield 34.0%

4-[1-(2-Hexylsulfanyl-6-methyl-pyrimidin-4-yl)-ethyl]-morpholine

Yield 34.0%

Solvents

tetraisopropyl orthotitanate

2-propanol

Conditions

Workup

1. 1
   ExtractionExtraction

Procedure

1-(2-Hexylsulfanyl-6-methyl-pyrimidin-4-yl)-ethanone (200 mg, 0.79 mmol) and morpholine (138 μL, 1.58 mol) were dissolved in tetraisopropyl orthotitanate (0.5 mL) and heated at 80° C. for 16 h. The brown solution was diluted with 2-propanol (5 mL) and treated with sodium cyanoborohydride (32 mg, 0.5 mmol) at 20° C. for 6 h. Extraction: 2×AcOEt, 2× sat. NH4Cl solution. Chromatography: Si-amine, heptane/ethyl acetate 85:15. One obtained 86 mg (34%) of a yellow oil. MS: m/z=324 (M+H).

Source