Reaction #985313

Reaction equation

Water

2-Hexylsulfanyl-6-methyl-pyrimidine-4-carbaldehyde

2,6-dimethylpiperidine

sodium cyanoborohydride

→

colorless liquid

Yield 36.0%

4-(2,6-Dimethyl-piperidin-1-ylmethyl)-2-hexylsulfanyl-6-methyl-pyrimidine

Yield 36.0%

Solvents

tetraisopropyl orthotitanate

2-propanol

Conditions

Workup

1. 1
   Filtrationthe resulting precipitate filtered off
2. 2
   Otherevaporated
3. 3
   ExtractionThe product was extracted with AcOEt, sat. NH4Cl solution
4. 4
   Otherdried
5. 5
   Concentrationconcentrated
6. 6
   OtherThe residue was purified by preparative HPLC chromatography on a YMC combiprep ODS-AQ column (75×20 mm iD

Procedure

2-Hexylsulfanyl-6-methyl-pyrimidine-4-carbaldehyde (0.2 g, 1 mmol) and 2,6-dimethylpiperidine (0.23 mL, 2 mmol) were dissolved in tetraisopropyl orthotitanate (0.5 mL) and stirred at 20° C. for 1 h. The solution was diluted with 2-propanol (5 mL) and treated with sodium cyanoborohydride (105 mg, 2 mmol) at 20° C. for 20 h. Water (1 mL) was added, and the resulting precipitate filtered off and evaporated. The product was extracted with AcOEt, sat. NH4Cl solution, dried and concentrated. The residue was purified by preparative HPLC chromatography on a YMC combiprep ODS-AQ column (75×20 mm iD, S-5 μM, 12 nm) with an acetonitrile-water gradient. One obtained 37 mg (36%) of a colorless liquid. MS: m/z=336 (M+H).

Source