4-Chloro-2-methoxy-6-methyl-5-nitropyrimidine → 2-Methoxy-4,6-dimethyl-5-nitropyrimidine

HRID 1398868Notes

Reaction equation

[Cl-].[CH3:2][Zn+].Cl[C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[C:9]([CH3:14])[N:8]=[C:7]([O:15][CH3:16])[N:6]=1>O1CCCC1.O>[CH3:16][O:15][C:7]1[N:8]=[C:9]([CH3:14])[C:10]([N+:11]([O-:13])=[O:12])=[C:5]([CH3:2])[N:6]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Methylzinc chloride (2.0 M solution in tetrahydrofuran, 14.8 mL, 29.6 mmol) was added dropwise to a solution of 4-chloro-2-methoxy-6-methyl-5-nitropyrimidine (4.01 g, 19.7 mmol) and tetrakis(triphenyl phosphine)palladium (2.20 g, 1.90 mmol) in tetrahydrofuran (60 mL) at 0° C., and the mixture was stirred at 50° C. for 50 minutes. The mixture was diluted with water, and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 5-20% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the title compound as a pale yellow solid (3-0.37 g, 18.4 mmol, 93%).

Workup

extractionextracted with ethyl acetate
washThe combined organic layer was washed with brine
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by flash column chromatography on silica gel eluting with a 5-20% ethyl acetate/n-hexane gradient mixture
concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-bcf564f0e4554ae1907b8567aef0f6e4
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901141B2

Reaction notes

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