Benzyl Chloride → 2-Amino-4-methyl-6-benzyloxypyrimidine

HRID 2058164Notes

Reaction equation

HRID 2058164 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[C:4]([OH:9])[N:3]=1.[H-].[Na+].[CH2:12](Cl)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C)C=O>[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[C:4]([O:9][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:3]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 178429408HCID 178429408, compound

Product 1

HCID 233498922-Amino-4-methyl-6-benzyloxypyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

2-Amino-4-methyl-6-hydroxypyrimidine (62.5 g, 0.50 mole) is dissolved in 500 ml of dimethylformamide and sodium hydride (0.5 mole) is added over a 1 hour period under a nitrogen atmosphere. The mixture is heated at 75° C. for 11/2 hours. Benzyl chloride (69.3 g, 0.55 moles) is then added over 15 minutes and the mixture is heated at 90° C. and stirred for 11/2 hours. After cooling, the reaction mixture is filtered and concentrated under vacuum to an oil from which 2-amino-4-methyl-6-benzyloxypyrimidine melting at 108°-109.5° C. is obtained by crystallization from n-butyl chloride.

Workup

  1. temperaturethe mixture is heated at 90° C.
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture is filtered
  4. concentrationconcentrated under vacuum to an oil from which 2-amino-4-methyl-6-benzyloxypyrimidine melting at 108°-109.5° C.
  5. customis obtained by crystallization from n-butyl chloride

Sources & evidence

ORD record
ord-2642e564231848eeaba0eb16290b3630
Source dataset
uspto-grants-1980_07
Patent number
US04215121

Reaction notes

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