Formamidine acetate → 5-(p-Methoxyphenoxy)pyrimidine

HRID 1413051Notes

Reaction equation

HRID 1413051 reaction equation
[Na].C(O)(=O)C.[CH:6]([NH2:8])=[NH:7].[CH3:9][O:10][C:11]1[CH:24]=[CH:23][C:14]([O:15][C:16](=[CH:19]N(C)C)[CH:17]=O)=[CH:13][CH:12]=1.[O-]CC.[Na+]>C(O)C>[CH3:9][O:10][C:11]1[CH:24]=[CH:23][C:14]([O:15][C:16]2[CH:17]=[N:7][CH:6]=[N:8][CH:19]=2)=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 160693Formamidine acetateHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 544980242-(p-Methoxyphenoxy)-3-(dimethylamino)acrolein

Product 1

HCID 202926325-(p-Methoxyphenoxy)pyrimidineYield 64.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium metal (4.1 g) was dissolved in absolute ethanol (90 ml) and formamidine acetate (18.4 g) and 2-(p-methoxyphenoxy)-3-(dimethylamino)acrolein (13.0 g) were added to the ethanolic solution of sodium ethoxide. The mixture was heated under reflux, with stirring, for 40 hr and then the solvent was removed, by distillation under reduced pressure. The residue was treated with water (200 ml) and chloroform (200 ml), the chloroform layer was separated and the chloroform removed by distillation under reduced pressure. The residue was purified by column chromatography over silica gel using chloroform as eluent to give 5-(p-methoxyphenoxy)pyrimidine as an oil (7.7 g) which was characterised by p.m.r. spectroscopy.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux
  3. customthe solvent was removed, by distillation under reduced pressure
  4. additionThe residue was treated with water (200 ml) and chloroform (200 ml)
  5. customthe chloroform layer was separated
  6. customthe chloroform removed by distillation under reduced pressure
  7. customThe residue was purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-7c9c18fa35224396956b3055bc705172
Source dataset
uspto-grants-1981_02
Patent number
US04248618

Reaction notes

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