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

HRID 898134Notes

Reaction equation

[CH2:1]([S:7][C:8]1[N:13]=[C:12]([CH:14]([OH:16])[CH3:15])[CH:11]=[C:10]([CH3:17])[N:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.OS(O)(=O)=O>CC(C)=O>[CH2:1]([S:7][C:8]1[N:13]=[C:12]([C:14](=[O:16])[CH3:15])[CH:11]=[C:10]([CH3:17])[N:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

Conditions

Temperature: 20 °C

Procedure

1-(2-Hexylsulfanyl-6-methyl-pyrimidin-4-yl)-ethanol (2.2 g, 8.65 mmol) was dissolved under nitrogen in acetone (20 mL). Then 2 M Jones' reagent prepared from 20 g CrO3 in 100 mL 4 M H2SO4 (6.5 mL, 13 mmol) was add dropwise. After stirring for 2 h at 20° C., the resulting green solution was decanted from the chromium salts and extracted with AcOEt and sat. NaCl solution. The crude product was purified by chromatography on silica gel with a heptane/AcOEt gradient. One obtained 960 mg (44 %) of white crystals. MS: m/z=252 (M).

Workup

additionwas add dropwise
customthe resulting green solution was decanted from the chromium salts
extractionextracted with AcOEt and sat. NaCl solution
customThe crude product was purified by chromatography on silica gel with a heptane/AcOEt gradient

Sources & evidence

ORD record: ord-203a9b8813974ef6b56ea1e9bbf0b63d
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07351700B2

Reaction notes

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