2-Chloro-5-nitropyrimidine → 2-Methoxy-5-nitropyrimidine

HRID 450179

Reaction equation

HRID 450179 reaction equation
[CH3:1][O-:2].[Na+].Cl[C:5]1[N:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][N:6]=1>CO>[CH3:1][O:2][C:5]1[N:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][N:6]=1

Participants

4

Reactant 2

HCID 825442-Chloro-5-nitropyrimidineHCID 10942334Sodium Methoxide

Product 1

HCID 3529002-Methoxy-5-nitropyrimidineYield 134.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of sodium methoxide (0.090 g of sodium) in MeOH (12 mL) was added 0.486 g (3.03 mmol) of 2-chloro-5-nitropyrimidine, and the mixture was heated under reflux for 1 hr. After cooling, the mixture was concentrated in vacuo, extracted with EtOAc, and washed with water. The aqueous layer was extracted with CHCl3 and the combined organic layers were dried (Na2SO4), and concentrated, to give 0.347 g (75% yield) of 2-methoxy-5-nitropyrimidine as a yellow powder: 1H NMR (CDCl3) δ9.31 (s, 2H), 4.17 (s, 3H); LCMS (APCI+) m/z: 156 (MH+, 100%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hr
  3. temperatureAfter cooling
  4. concentrationthe mixture was concentrated in vacuo
  5. extractionextracted with EtOAc
  6. washwashed with water
  7. extractionThe aqueous layer was extracted with CHCl3
  8. dry with materialthe combined organic layers were dried (Na2SO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-160f4f9dca0f416a938b965dced57a0a
Source dataset
uspto-grants-2013_07
Patent number
US08486939B2

Linked notes

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