ChemicalBook CAS DataBase List Diaveridine

Diaveridine synthesis

5synthesis methods

Product Name:Diaveridine
CAS Number:5355-16-8
Molecular formula:C13H16N4O2
Molecular Weight:260.29

91-16-7
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7440-44-0 Synthesis

7440-44-0
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54236-98-5
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5355-16-8
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Yield:5355-16-8 88.7%

Reaction Conditions:

with potassium hydroxide;sodium hydroxide;phosphoric acid in water;acetic acid

Steps:

4 Preparation of 2,4-diamino-5-(3,4-dimethoxybenzyl)pyrimidine
EXAMPLE 4 Preparation of 2,4-diamino-5-(3,4-dimethoxybenzyl)pyrimidine A mixture of 12.3 g. of 2,4-diamino-5-methoxymethylpyrimidine, 10.9 g. of veratrole and 72 g. of orthophosphoric acid was stirred and heated at 110° for 4 hours. The resulting thick yellow solution was dissolved in 40 ml. of water and the formed solution slowly added to 190 ml. of a 50 percent potassium hydroxide solution at 10°-15°. A white precipitate formed and the mixture was allowed to digest in the refrigerator overnight. The precipitate was removed by filtration and the solid washed with ice water until the washings reached a pH 8. The product was then dissolved in a solution comprised of 50 ml. of glacial acetic acid and 175 ml. of water. The resulting yellow turbid solution was treated with charcoal and filtered. The resudue was washed with 100 ml. of water. The aqueous solutions were combined and treated dropwise at 0° with 190 ml. of a solution prepared from 40 g. of sodium hydroxide and 200 ml. of water. The precipitate was removed by filtration, washed with water and air-dried to give 17.2 g. of 2,4-diamino-5-(3,4-dimethoxybenzyl)pyrimidine (88.7 percent) having a melting point of 227°-230°.

References:

Hoffmann-La Roche Inc. US4143227, 1979, A

FullText

50-01-1 Synthesis