2,4-Dichloro-5-nitropyrimidine → 2-Chloro-4-methoxy-5-nitropyrimidine

HRID 390292Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[CH3:12][O-:13].[K+]>CO>[Cl:1][C:2]1[N:7]=[C:6]([O:13][CH3:12])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2,4-dichloro-5-nitropyrimidine (10 g, 51.55 mmol) in methanol (150 ml) at −10° C. a solution of potassium methanolate (3.62 g, 51.55 mmol) in methanol (150 ml) was added over a period of 10 minutes. The mixture was allowed to warm to 0° C. and the solvent was evaporated under reduced pressure at 30° C. The residue was purified by silica gel chromatography with n-heptane/ethyl acetate (3:1) as eluent affording 3.7 g (37.9%) of the title compound. 1.34 g (13.7%) 4-chloro-2-methoxy-5-nitropyrimidine was obtained as a side product

Workup

customthe solvent was evaporated under reduced pressure at 30° C
customThe residue was purified by silica gel chromatography with n-heptane/ethyl acetate (3:1) as eluent

Sources & evidence

ORD record: ord-209653b29e3545e2b6c8776e1aa72fa8
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383641B2

Reaction notes

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