N,N-Dimethylaniline → HCID 18982107, compound

HRID 1440886Notes

Reaction equation

HRID 1440886 reaction equation
[CH2:1]([O:3][C:4]1[C:9]([NH:10][C:11]([C:13]2[O:14][CH:15]=[CH:16][CH:17]=2)=O)=[C:8]([OH:18])[N:7]=[C:6]([CH3:19])[N:5]=1)[CH3:2].CN(C)C1C=CC=CC=1>P(Cl)(Cl)(Cl)=O>[CH2:1]([O:3][C:4]1[C:9]2[N:10]=[C:11]([C:13]3[O:14][CH:15]=[CH:16][CH:17]=3)[O:18][C:8]=2[N:7]=[C:6]([CH3:19])[N:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 949N,N-DimethylanilineHCID 178467434HCID 178467434, compound

Product 1

HCID 18982107HCID 18982107, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A mixture of 4-ethoxy-5-(2-furanylcarbonyl)amino-6-hydroxy-2-methylpyrimidine (2.07 g, 7.87 mM), phosphorus oxychloride (30 ml) and dimethylaniline (1.5 ml, 11.7 mM) was heated at reflux for one hour. After cooling, the excess phosphorus oxychloride was removed by distillation under reduced pressure. Ethanol was then added, and the mixture partitioned between methylene chloride and water. The organic layer was separated, washed with sodium bicarbonate, water, dilute hydrochloric acid, water, and dried. The solvent was then removed by distillation under reduced pressure. Ethanol (10 ml) was added and the solid filtered off. This solid was further purified by flash column chromatography eluting with ethyl acetate/hexane (1:3). There was thus produced 7-ethoxy-5-methyl-2-(2-furyl)-oxazolo[5,4-d]pyrimidine (1.49 g, 77% yield); m.p. 104°-105.5° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for one hour
  3. temperatureAfter cooling
  4. customthe excess phosphorus oxychloride was removed by distillation under reduced pressure
  5. additionEthanol was then added
  6. customthe mixture partitioned between methylene chloride and water
  7. customThe organic layer was separated
  8. washwashed with sodium bicarbonate, water, dilute hydrochloric acid, water
  9. customdried
  10. customThe solvent was then removed by distillation under reduced pressure
  11. additionEthanol (10 ml) was added
  12. filtrationthe solid filtered off
  13. customThis solid was further purified by flash column chromatography
  14. washeluting with ethyl acetate/hexane (1:3)

Sources & evidence

ORD record
ord-102279031861402b87087005764947f5
Source dataset
uspto-grants-1996_03
Patent number
US05500428

Reaction notes

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