HCID 19097735, compound → 5-Amino-2-(2-propoxyphenyl)-4(3H)-pyrimidinone

HRID 486239Notes

Reaction equation

HRID 486239 reaction equation
[N+:1]([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.[H][H]>CO.[Pd]>[NH2:1][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

Participants

5

Reactant 2

HCID 19097735HCID 19097735, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 190977375-Amino-2-(2-propoxyphenyl)-4(3H)-pyrimidinone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 5-nitro-2-(2-propoxyphenyl)-pyrimidin-4(3H)-one (4.34 g) in methanol (120 ml) was treated with hydrogen at atmospheric pressure and ambient temperature in the presence of 10% palladium on carbon (170 mg) for five hours. The reaction mixture was filtered and the filtrate was evaporated under reduced pressure affording a dark oily residue. This was eluted from a silica column with chloroform and the combined fractions containing product were evaporated under reduced pressure to afford the crude title compound as a dark yellow solid, 1.69 g. This was recrystallised from isopropylacetate, then dissolved in boiling 2 Normal hydrochloric acid, and the filtered, cooled solution was washed with chloroform. The acidic solution was neutralised with potassium carbonate which afforded a pale yellow solid, 600 mg, which was recrystallised from acetonitrile to afford the title compound, 250 mg, m.p. 157°-158° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated under reduced pressure
  3. customaffording a dark oily residue
  4. washThis was eluted from a silica column with chloroform
  5. additionthe combined fractions containing product
  6. customwere evaporated under reduced pressure
  7. customto afford the crude title compound as a dark yellow solid, 1.69 g
  8. customThis was recrystallised from isopropylacetate
  9. dissolutiondissolved
  10. temperaturethe filtered, cooled solution
  11. washwas washed with chloroform
  12. customafforded a pale yellow solid, 600 mg, which
  13. customwas recrystallised from acetonitrile

Sources & evidence

ORD record
ord-d8584917e356479ca50698f34265cb34
Source dataset
uspto-grants-1994_03
Patent number
US05290933

Reaction notes

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