Methane → 2-(2-Propoxyphenyl)pyrimidin-4(3H)-one

HRID 486241Notes

Reaction equation

HRID 486241 reaction equation
C([C:4]1[C:5](=[O:20])[NH:6][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH2:17][CH2:18][CH3:19])=[N:8][CH:9]=1)(O)=O.CCOCC.C>N1C2C(=CC=CC=2)C=CC=1.C(O)C>[CH2:17]([O:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C:7]1[NH:6][C:5](=[O:20])[CH:4]=[CH:9][N:8]=1)[CH2:18][CH3:19]

Participants

6

Reactant 3

HCID 297MethaneHCID 3283Diethyl EtherHCID 125358445-Carboxy-2-(2-propoxyphenyl)pyrimidin-4(3H)-one

Product 1

HCID 212020502-(2-Propoxyphenyl)pyrimidin-4(3H)-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 7047QuinolineSolvent

Procedure

5-Carboxy-2-(2-propoxyphenyl)pyrimidin-4(3H)-one (2.03 g, U.S. Pat. No. 4,031,093) in quinoline (10 ml) was heated under reflux under nitrogen for two hours. Ether was added to the cooled reaction mixture which was then extracted with aqueous sodium hydroxide. The basic extract was washed with ether and then acidified with concentrated hydrochloric acid to pH 7. The aqueous mixture was extracted with chloroform and the chloroform extract was washed with aqueous hydrochloric acid, dried and evaporated under reduced pressure to afford a yellow solid. This solid was dissolved in ethanol and the ethanolic solution Was treated with charcoal, filtered and reduced in volume. From this precipitated a yellow solid impurity which was removed by filtration. A small quantity of the crude title compound (0.1 g) precipitated from the filtrate, however this together with another sample of crude title compound (0.54 g) similarly prepared was combined with the filtrate and eluted from a silica column with chloroform. Combined fractions containing product were evaporated under reduced pressure to afford a solid, 270 mg, which was recrystallised from ether to afford the title compound, 170 mg, m.p. 112°-113° C.

Workup

  1. temperatureunder reflux under nitrogen for two hours
  2. extractionwas then extracted with aqueous sodium hydroxide
  3. extractionThe basic extract
  4. washwas washed with ether
  5. extractionThe aqueous mixture was extracted with chloroform
  6. extractionthe chloroform extract
  7. washwas washed with aqueous hydrochloric acid
  8. customdried
  9. customevaporated under reduced pressure
  10. customto afford a yellow solid
  11. filtrationfiltered
  12. customFrom this precipitated a yellow solid impurity which
  13. customwas removed by filtration
  14. customA small quantity of the crude title compound (0.1 g) precipitated from the filtrate
  15. customhowever this together with another sample of crude title compound (0.54 g) similarly prepared
  16. washeluted from a silica column with chloroform
  17. additionCombined fractions containing product
  18. customwere evaporated under reduced pressure
  19. customto afford a solid, 270 mg, which
  20. customwas recrystallised from ether

Sources & evidence

ORD record
ord-7d20694332394d7ba111069f08609f44
Source dataset
uspto-grants-1994_03
Patent number
US05290933

Reaction notes

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