Reaction #985312

Reaction equation

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

pyrrolidine

sodium cyanoborohydride

→

yellow liquid

Yield 28.2%

2-Hexylsulfanyl-4-methyl-6-pyrrolidin-1-ylmethyl-pyrimidine

Yield 28.2%

Solvents

ethanol

acetic acid

Conditions

Workup

1. 1
   OtherThe reaction mixture was evaporated to dryness
2. 2
   workup.DISSOLUTIONdissolved in a minimal amount of DMF (0.8 mL)
3. 3
   Otherdirectly purified by preparative HPLC chromatography on a YMC combiprep ODS-AQ column (75×20 mm iD

Procedure

2-Hexylsulfanyl-6-methyl-pyrimidine-4-carbaldehyde (0.1 g, 0.42 mmol) was dissolved in ethanol (1 mL) and acetic acid (0.1 mL). Then pyrrolidine (0.07 mL, 1 mmol) and sodium cyanoborohydride (26 mg, 0.4 mmol) were added slowly at 20° C. and stirring continued for 24 h. The reaction mixture was evaporated to dryness and dissolved in a minimal amount of DMF (0.8 mL) and directly 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 34.7 mg (28%) of a yellow liquid. MS: m/z=294 (M+H).

Source