Reaction #312618

Reaction equation

4,6-dichloro-2-methanesulfonyl-pyrimidine

sodium hydride

4-acetamidophenol

→

title compound

Yield 95.3%

N-[4-(4,6-Dichloro-pyrimidin-2-yloxy)-phenyl]-acetamide

Yield 95.3%

Solvents

NH4Cl

EtOAc

THF

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   OtherThe organic layer was separated
3. 3
   Washwashed with saturated aqueous NaCl
4. 4
   Dryingdried over sodium sulfate
5. 5
   Concentrationthen concentrated in vacuo
6. 6
   OtherThe residue was purified by column chromatography (Silica Gel, MeOH:CH2Cl2, 5:95)

Procedure

A solution of 4-acetamidophenol (666 mg, 4.40 mmol) in anhydrous THF (40 ml), stirring at ambient temperature, was treated with a 60% dispersion of sodium hydride in mineral oil (176 mg, 4.40 mmol). The reaction mixture was then allowed to stir for 30 minutes at ambient temperature before 4,6-dichloro-2-methanesulfonyl-pyrimidine (1.0 g, 4.40 mmol) was added. The reaction was then allowed to stir for a further 3 hours before the reaction was diluted with saturated aqueous NH4Cl and EtOAc. The organic layer was separated, washed with saturated aqueous NaCl and dried over sodium sulfate then concentrated in vacuo. The residue was purified by column chromatography (Silica Gel, MeOH:CH2Cl2, 5:95) yield the title compound 1.25 g, (95%) as a solid. 1H-NMR (400 MHz, DMSO-d6): δ 2.06 (3 H, s), 7.18 (2 H, d, J=8.5 Hz), 7.62 (2 H, d, J=8.5 Hz), 10.05 (1 H, s), LC-MS: ES+=298.16, ES−=296.18).

Source