Abstract
When 6-chloro-2, 4-dimethoxypyrimidine (I) was reacted with sodium amide in liquid ammonia, 2-amino-4, 6-dimethoxypyrimidine (III) was afforded in 47% yield, besides a small amount of by-products, such as 4-methoxy-2, 6-diaminopyrimidine (VIII), 2-methoxy-4, 6-diaminopyrimidine (IX), as well as 6-amino-2, 4-dimethoxyprimidine (II), which has been expected to be main product.It was found that in liquid ammonia, (I) was reacted with sodium methylate to 2, 4, 6-trimethoxypyrimidine (VII) and that (VII) was reacted with sodium amide to (III) in better yield, respectively. 2-Amino-4-methoxy-6-chloropyrimidine (VI) was reacted with sodium amide to (VIII) in liquid ammonia.Considering from the results, the reaction mechanism from (I) to (III) has been suggested that the CH3O- group which was attacked by sodium amide at either 2 or 4 position of (I) was reacted with the non-reacted (I) to yield (VII), followed by the secondary reaction between (VII) and excess sodium amide into (III).
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