Propylamine → 5-(2,4-Dimethylphenyl)-3-methyl-2-propylaminopyrimidin-4(3H)-one

HRID 598084Notes

Reaction equation

HRID 598084 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10](=[O:18])[N:11]([CH3:17])[C:12](SC)=[N:13][CH:14]=1.[CH2:19]([NH2:22])[CH2:20][CH3:21]>>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10](=[O:18])[N:11]([CH3:17])[C:12]([NH:22][CH2:19][CH2:20][CH3:21])=[N:13][CH:14]=1

Participants

3

Reactant 2

HCID 7852PropylamineHCID 589385625-(2,4-Dimethylphenyl)-3-methyl-2-(methylthio)pyrimidin-4(3H)-one

Product 1

HCID 589385915-(2,4-Dimethylphenyl)-3-methyl-2-propylaminopyrimidin-4(3H)-oneYield 67%

Conditions

Temperature
100 °C

Procedure

To a sealed tube was added 0.15 g (0.57 mmol) of 5-(2,4-dimethyl-phenyl)-3-methyl-2-(methylthio)pyrimidin-4(3H)-one and 3 ml (50 mmol) of propyl amine. The mixture was heated to 100° C. for 48 h. The reaction was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and washed with saturated sodium bicarbonate. The organic phase was dried over magnesium sulfate. Filtration, removal of solvent and purification of the residue via biotage eluting with 50% ethyl acetate/hexanes gave 0.1 g (67%) of product.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with saturated sodium bicarbonate
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. filtrationFiltration, removal of solvent and purification of the residue via biotage
  6. washeluting with 50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-a1cb67b02dcf4ee28c2e7fc328e58e58
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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