6-Amino-2-(2-propoxyphenyl)pyrimidin-4[3H]-one → 6-Butyramido-2-(2-propoxyphenyl)pyrimidin-4[3H1 one

HRID 892432Notes

Reaction equation

HRID 892432 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[O:14][CH2:15][CH2:16][CH3:17])[NH:5][C:4](=[O:18])[CH:3]=1>C(O)C>[C:9]([NH:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[O:14][CH2:15][CH2:16][CH3:17])[NH:5][C:4](=[O:18])[CH:3]=1)(=[O:14])[CH2:8][CH2:13][CH3:12]

Participants

3

Reactant 1

HCID 1355065006-Amino-2-(2-propoxyphenyl)pyrimidin-4[3H]-one

Product 1

HCID 1354821756-Butyramido-2-(2-propoxyphenyl)pyrimidin-4[3H1 one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of 6-amino-2-(2-propoxyphenyl)-pyrimidin-4[3H]-one (0.68 g) and n-butyric anhydri was heated at 140° C. for 5 hours. Ethanol was added to the cooled reaction mixture which was then evaporated under reduced pressure to yield a residue which was azeotroped and washed with water. The residue was eluted from silica with chloroform and the combined fractions containing product were evaporated under reduced pressure to yield a crude product which was recrystallised from isopropanol: diethyl ether to yield the title compound, 0.21 g, m.p. 177°-8° C.

Workup

  1. customwas then evaporated under reduced pressure
  2. customto yield a residue which
  3. customwas azeotroped
  4. washwashed with water
  5. washThe residue was eluted from silica with chloroform
  6. additionthe combined fractions containing product
  7. customwere evaporated under reduced pressure
  8. customto yield a crude product which
  9. customwas recrystallised from isopropanol

Sources & evidence

ORD record
ord-2c5013dd9a8a413b8bf9c6bf42b322a5
Source dataset
uspto-grants-1992_06
Patent number
US05118686

Reaction notes

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