Chloromethylenedimethylammonium chloride

The main agent used for the conversion of oxopurine into chloropurines is phosphoryl chloride, either alone or with added water (which may produce pyrophosphoryl chloride), phosphorus pentachloride, or with bases, usually tertiary amines and especially W,W-dimethyl- or diethyl-aniline. The use of bases, especially aliphatic amines, may however lead to introduction of dialkyamino groups into the purine or formation of other byproducts (74RCR1089). Other reagents which have been used include (a) thionyl chloride in DMF (Vilsmeier-Haak reagents) which converts 2, 3, 5 -tri-0-benzoylinosine into the 6-chloropurine nucleoside (64CPB639) and (b) chloromethylenedimethylammonium chloride in chloroform. 

Other reagents used include thionyl chloride/dimethylformamide, e.g. formation of 8, and chloromethylenedimethylammonium chloride in chloroform, e.g. formation of... 

Uridine heated 8 hrs. at 120° with chloromethylenedimethylammonium chloride in dimethylformamide -> 5 -deoxy-5 -dilorouridine. Y 80%. - No isomeric by-prod-... 

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