Methyl iodide → 2-Amino-3-methyl-6-phenyl-4-pyrimidinone

HRID 1785440Notes

Reaction equation

HRID 1785440 reaction equation
[OH-].[K+].[CH3:3]I.[NH2:5][C:6]1[NH:11][C:10](=[O:12])[CH:9]=[C:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:7]=1>CCO>[NH2:5][C:6]1[N:11]([CH3:3])[C:10](=[O:12])[CH:9]=[C:8]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 14797Potassium HydroxideHCID 1354203652-Amino-6-phenylpyrimidin-4-ol

Product 1

HCID 133205052-Amino-3-methyl-6-phenyl-4-pyrimidinone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of KOH (1.22 g, 22 mmol), MeI (6.85 g, 48 mmol), and 2-amino-6-phenyl-3H-pyrimidin-4-one (2.62 g, 14 mmol) in EtOH (130 mL) was stirred at room temperature in a stoppered 250 mL roundbottom flask for 3 days. An additional 6.85 g (48 mmol) MeI was added and stirring was continued for 1 day. The solvent was removed under vacuum and the residue was dissolved in H2O (35mL), warmed to 50° C., and 1N HCl was added dropwise until the solid dissolved completely. The solution was cooled to room temperature, made slightly basic with saturated NaHCO3, and the resulting white solid was filtered and dried under vacuum. M+1: 202.

Workup

  1. stirringstirring
  2. waitwas continued for 1 day
  3. customThe solvent was removed under vacuum
  4. dissolutionthe residue was dissolved in H2O (35mL)
  5. temperaturewarmed to 50° C.
  6. addition1N HCl was added dropwise until the solid
  7. dissolutiondissolved completely
  8. temperatureThe solution was cooled to room temperature
  9. filtrationthe resulting white solid was filtered
  10. customdried under vacuum

Sources & evidence

ORD record
ord-39cb08f716ea46fc9d7265a15ce12e7a
Source dataset
uspto-grants-2009_03
Patent number
US07504403B2

Reaction notes

Loading…