Phosphorus oxychloride → HCID 21941670, compound

HRID 2216300Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:12]2[C:13](O)=[N:14][C:15]([CH3:18])=[N:16][CH:17]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.P(Cl)(Cl)([Cl:22])=O>>[Cl:22][C:13]1[C:12]([S:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)(=[O:11])=[O:10])=[CH:17][N:16]=[C:15]([CH3:18])[N:14]=1

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 178492803HCID 178492803, compound

Product 1

HCID 21941670HCID 21941670, compoundYield 83%

Procedure

A mixture of 5-(4-methoxy-benzenesulfonyl)-2-methyl-pyrimidin-4-ol (200 mg, 0.714 mmol) in phosphorus oxychloride (4 mL) was refluxed under N2 for 2 h and then cooled to room temperature. Solvents were removed in vacuo, and the residue was poured into ice water with stirring. The mixture was neutralized with saturated sodium bicarbonate to pH˜7 and extracted with methylene chloride (3×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel (1:1 ethyl acetate/hexanes) to provide 4-chloro-5-(4-methoxy-benzenesulfonyl)-2-methyl-pyrimidine (177 mg, 83%) as a light yellow solid: 1H NMR (300 MHz, CDCl3) δ 9.32 (s, 1H), 7.93 (d, J=7.2 Hz, 2H), 7.01 (d, J=7.2 Hz, 2H), 3.89 (s, 3H), 2.77 (s, 3H); ESI MS m/z 299 [(M+H)+, calcd for C12H12ClN2O3S, 299.0].

Workup

temperaturewas refluxed under N2 for 2 h
customSolvents were removed in vacuo
additionthe residue was poured into ice water
extractionextracted with methylene chloride (3×)
washThe combined organic layers were washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by chromatography on silica gel (1:1 ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-7c1252c5bf0f4478ad8a51630ad6e3c7
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07112585B2

Reaction notes

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