Reaction #985314

Reaction equation

2-Hexylsulfanyl-6-trifluoromethyl-pyrimidine-4-carbaldehyde

morpholine

acetic acid

→

expected product

4-(2-Hexylsulfanyl-6-trifluoromethyl-pyrimidin-4-ylmethyl)-morpholine

Solvents

ethanol

Conditions

Workup

1. 1
   OtherThe reaction mixture was evaporated to dryness
2. 2
   ExtractionExtraction
3. 3
   OtherOne obtained

Procedure

2-Hexylsulfanyl-6-trifluoromethyl-pyrimidine-4-carbaldehyde (0.5 g, 1.7 mmol) and morpholine (0.16 mL, 1.9 mmol) were dissolved in ethanol (5 mL) and acetic acid (0.5 mL) and treated with borane-pyridine complex (0.19 mL, 1.9 mmol) for 4 h at 20° C. The reaction mixture was evaporated to dryness. Extraction: 2×AcOEt, 1×10% aqueous Na2CO3. One obtained a mixture of the expected product and the reduced aldehyde which was more polar. This mixture was separated by chromatography on Si-amine from Silicycle with a gradient of heptane/ethyl acetate from 10:1 up to 1:1. Gave 220 mg (35%) of a colorless oil. MS: m/z=364 (M+H).

Source