Potassium Hydroxide → 5-(2,4-Dimethylphenyl)-2-(dipropylamino)-3-methylpyrimidin-4(3H)-one

HRID 598085Notes

Reaction equation

HRID 598085 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:20])[N:11]([CH3:19])[C:12]([NH:15][CH2:16][CH2:17][CH3:18])=[N:13][CH:14]=1.[OH-].[K+].I[CH2:24][CH2:25][CH3:26]>O1CCCC1.C(OCC)(=O)C>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10](=[O:20])[N:11]([CH3:19])[C:12]([N:15]([CH2:24][CH2:25][CH3:26])[CH2:16][CH2:17][CH3:18])=[N:13][CH:14]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 336431-IodopropaneHCID 589385915-(2,4-Dimethylphenyl)-3-methyl-2-propylaminopyrimidin-4(3H)-one

Product 1

HCID 589386035-(2,4-Dimethylphenyl)-2-(dipropylamino)-3-methylpyrimidin-4(3H)-oneYield 65%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution containing 0.2 g (0.74 mmol) of 5-(2,4-dimethylphenyl)-3-methyl-2-propylaminopyrimidin-4(3H)-one in 5 ml of tetrahydrofuran under a nitrogen atmosphere was added 0.12 g (2.2 mmol) of potassium hydroxide followed by 0.38 g (2.2 mmol) of 1-iodopropane. The reaction was allowed to stir at room temperature for 12 h, diluted with 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 chromatography eluting with 30% ethyl acetate/dichloromethane gave 0.15 g (65%) of product.

Workup

  1. washwashed with saturated sodium bicarbonate
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. filtrationFiltration, removal of solvent and purification of the residue via Biotage chromatography
  4. washeluting with 30% ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-edc5335269fa4645afc010d164350cc9
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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