132138-67-1Relevant articles and documents
Facile synthesis of 9-substituted 9-deazapurines as potential purine nucleoside phosphorylase inhibitors.
Shih, Hsiencheng,Cottam, Howard Brinkerhoff,Carson, Dennis Anthony
, p. 364 - 367 (2007/10/03)
A facile synthesis of 9-substituted 9-deazapurines as potential inhibitors of purine nucleoside phosphorylase has been achieved by the direct Friedel-Crafts aroylation or arylmethylation of 9-deazapurines using trifluoromethanesulfonic acid as catalyst. The aroylated 9-deazapurines could be transformed into the corresponding 9-aryimethyl derivatives by the Wolff-Kishner reaction. A novel synthesis of 9-deazahypoxanthine was also developed by treatment of 4-hydroxy-5-phenylazo-6-methylpyrimidin-2-thione with triethyl orthoformate in trifluoroacetic acid (TFA) to yield 8-oxo-7H-2-phenylpyrimido[5,4-c]pyridazin-6-thione followed by Raney nickel reduction.
An Improved Synthesis of 7-Substituted Pyrrolo[3,2-d]pyrimidines
Elliott, Arthur J.,Morris Jr., Philip E.,Petty, Sandra L.,Williams, Carl H.
, p. 8071 - 8075 (2007/10/03)
Base (NaOMe)-catalyzed condensation of 3,3-dimethoxypropionitrile with aldehydes followed by hydrolysis with 6 N HCl gives the unsaturated cyano aldehydes 5. Catalytic reduction of the double bond followed by reaction with diethyl aminomalonate affords the enamines 7, which cyclize to the aminopyrroles 2 on treatment with NaOMe. While the amino group in 2 is unreactive toward many guanylating reagents, acid (AcOH)-catalyzed guanylation occurs easily with 10 to give 12 along with methyl mercaptan as a byproduct. Subsequent facile removal of the carbamate groups and ring closure to the pyrrolo[3,2-d]pyrimidine ring system occurs on treatment with base. The use of HgCl2 in place of AcOH ties up the mercaptan and eliminates the odor problem. For larger scale reactions where the mercaptan odor and the use of Hg salts are undesirable, the use of the methoxy analogue 11 is preferred. Using this procedure, benzaldehyde has been converted to the 7-(phenylmethyl)pyrrolo[3,2-d]pyrimidine (1a), a potent inhibitor of the enzyme purine nucleoside phosphorylase, in 31% overall yield with only three isolation steps.
Synthesis of pyrrolo[3,2-d]pyrimidines (9-deazaguanines) by reductive cyclodeamination reactions
Elliott, Arthur J.,Kotian, Pravin L.,Montgomery, John A.,Walsh, David A.
, p. 5829 - 5830 (2007/10/03)
An efficient synthesis of 9-deazaguanines by reductive cyclodeamination of 5-nitro-6-cyanomethylpyrimidine derivatives under acidic conditions is described.