2,4-Diamino-5-(4-methoxybenzyl)pyrimidine synthesis

Yield:20285-70-5 57%

Reaction Conditions:

with potassium hydroxide;sodium methylate in methanol;2-(2-methoxyethoxy)ethyl alcohol;2-methyl-propan-1-ol;water;

Steps:

1 2,4-Diamino-5-(4-methoxy-benzyl)-pyrimidine

EXAMPLE 1 2,4-Diamino-5-(4-methoxy-benzyl)-pyrimidine A mixture of 27.2 g (0.2 mole) of 4-methoxy-benzaldehyde (Fluka 10440), 2.5 g of 3-methoxy-propionitrile, 70 ml of methanol and 3 g of potassium hydroxide is stirred at 60° C. for 8 hours, whereupon the reaction mixture is cooled, diluted with 500 ml of water and extracted twice with 100 ml of benzene each. The organic layer is dried and evaporated in vacuo. The residue is dissolved in 50 ml of diethylene glycol monomethyl ether, then 3 g of powdered sodium methylate are added, the mixture is heated to 75°-77° C. and stirred at this temperature for 3 hours. To the mixture 80 ml of isobutanol, 53 g of guanidine hydrochloride and a 30% methanolic solution of 27 g of sodium methylate are added. The reaction mixture is heated to 92° C. whereby methanol is distilled off. The reaction mixture is heated at this temperature for 7 hours, then cooled, the precipitated crystals are filtered and recrystallized from aqueous ethanol. Thus 23.2 g of the desired compound are obtained, yield 57%. M.p.: 206°-209° C. Analysis for the Formula C₁₂ H₁₄ N₄ O: calculated: C%=62.59; H%=6.13; N%=24.33; found: C%=62.61; H%=5.96; N%=24.21.

References:

US4883798,1989,A