Reaction #985310

Reaction equation

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

HCl

Na2CO3

→

yellow oil

Yield 94.6%

6-Cyclopropyl-2-hexylsulfanyl-pyrimidine-4-carbaldehyde

Yield 94.6%

Solvents

THF

Conditions

Workup

1. 1
   Extractionextracted twice with AcOEt and once with sat. NaCl solution
2. 2
   OtherThe crude product was purified by chromatography on silica gel in heptane/DCM with a gradient of 100:0 to 67:33

Procedure

4-Cyclopropyl-6-diethoxymethyl-2-hexylsulfanyl-pyrimidine (2.7 g, 8 mmol) was dissolved in THF (13 mL) and 4 N HCl (13 mL) and stirred at 20° C. for 19 h. The reaction mixture was poured in cold 10% Na2CO3 (100 mL) and extracted twice with AcOEt and once with sat. NaCl solution. The crude product was purified by chromatography on silica gel in heptane/DCM with a gradient of 100:0 to 67:33. One obtained 2 g (94%) of a yellow oil, which solidified upon standing in the fridge. MS: m/z=264 (M).

Source