2,4-Dichloro-6-methyl-5-nitropyrimidine → 2-Chloro-4-methoxy-6-methyl-5-nitropyrimidine

HRID 598058Notes

Reaction equation

HRID 598058 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([N+:9]([O-:11])=[O:10])=[C:4]([CH3:12])[N:3]=1.[CH3:13][O-:14].[Na+]>CO>[Cl:1][C:2]1[N:7]=[C:6]([O:14][CH3:13])[C:5]([N+:9]([O-:11])=[O:10])=[C:4]([CH3:12])[N:3]=1

Participants

4

Reactant 2

HCID 2752942,4-Dichloro-6-methyl-5-nitropyrimidineHCID 10942334Sodium Methoxide

Product 1

HCID 130809792-Chloro-4-methoxy-6-methyl-5-nitropyrimidineYield 65.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-10 °C

Procedure

2,4-Dichloro-6-methyl-5-nitropyrimidine (3.0 g, 14.4 mmol) was dissolved in methanol (30 mL). The solution was cooled to −10° C. and sodium methoxide (25% in methanol, 3.3 mL, 14.4 mmol) was added drop wise. After 10 minutes, the solution was quenched with acetic acid (5 mL) and concentrated. The residue was suspended in saturated sodium bicarbonate and extracted twice with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and concentrated. Flash chromatography (5% ethyl acetate/hexanes) gave 1.91 g (65% yield) of the title compound as a white solid.

Workup

  1. customthe solution was quenched with acetic acid (5 mL)
  2. concentrationconcentrated
  3. extractionextracted twice with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-29520bfb21f447d98738019874294ace
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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