Sodium Methoxide → 4-Chloro-6-methoxy-2-(methylthio)-5-nitropyrimidine

HRID 550847Notes

Reaction equation

HRID 550847 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6](Cl)[N:5]=[C:4]([S:12][CH3:13])[N:3]=1.[CH3:14][O-:15].[Na+]>CO>[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([O:15][CH3:14])[N:5]=[C:4]([S:12][CH3:13])[N:3]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 113454584,6-Dichloro-2-(methylthio)-5-nitropyrimidine

Product 1

HCID 215176834-Chloro-6-methoxy-2-(methylthio)-5-nitropyrimidineYield 85.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4,6-Dichloro-2-methylthio-5-nitropyrimidine (5.25 g, 21.88 mmol) in methanol (40 mL) was treated with sodium methoxide (1.3 g, 24.06 mmol). The mixture was stirred at room temperature for 3 h. At this point the reaction was poured onto ice to give a brown solid which was filtered and washed with water. The solid was dried under vacuo to give 4-Chloro-6-methoxy-2-methylthio-5-nitropyrimidine (4.40 g, 85%) as a brown solid. LRMS for C6H6Cl1N3O3S (M+H)+ at m/z=235. The NMR spectrum obtained on the sample is compatible with its structure.

Workup

  1. additionAt this point the reaction was poured onto ice
  2. customto give a brown solid which
  3. filtrationwas filtered
  4. washwashed with water
  5. customThe solid was dried under vacuo

Sources & evidence

ORD record
ord-f01590ac05ff409a8d27cb3c0ed61961
Source dataset
uspto-grants-2011_05
Patent number
US07947692B2

Reaction notes

Loading…