المستخلص: |
Ethyl 5-amino-4-methyl-2-phenylfuro[2,3-d]pyrimidine–6-carboxylate (1) was used as precursor for the synthesis of pyrimido furoppyrimidines 2 , 3 and fur pyrimidine derivative4 by reaction withphenyl isothiocyanate , form amide and hydrazine hydrate respectively .Also Saponification of compound 1 followed by treatment with orthophosphoric acid afforded compound6 which underwent condensation with 4- methoxybenzaldehyde to give 6-arylidene-4-methyl-2-phenylfuro[2,3-d]pyrimidin-5- one(7) . On the other hand refluxing of compound 5 with acetic anhydride gave 5- N,Ndiacetylamino)- 4-methyl-2-phenylfuro[2,3-d]pyrimidine (9), which on treatment with hydrazine hydrate afforded N-acetyl amino derivative 10 .Chlorination of compound 3 with phosphorus oxychloride gave 8-Chloro-4-methyl-2-phenylpyrimido[4,5:4,5]furo[2,3-d]pyrimidine (11),which up on treatment with hydrazine hydrate gave the corresponding hydrazine derivatives 12. Condensation of compound 4 with 4-nitrobenzaldehydes gave 5- Amino-6-(4-nitrobenzylidene)-4-methyl-2-phenylfuro[2,3-d]pyrimidine-6-carbohydrazone (13).On the other hand refluxing of carbohydrazide 4 with formic acid and acetic anhydride led to the formation of compounds 14 and 15 respectively. Also 3,5-dimethyl parazolyl derivative 16 was prepared from the reaction of compound 4 with acetyl acetone . Treatment of compound1with 2,5-dimethoxytetrahydrofuran produced the compound17,which reacted with hydrazine hydrate to give carbohydrazide derivative18. The reaction of 18 with CS2followed by methyl iodide gave the 6-(2-methylthio-1,3,4-oxadiazol-5-yl)-4-methyl-5-(1-pyrrolyl)-2-phenylfuro[2,3-d]pyrimidine ( 20 ). On the other handcompounds21 and 22 were obtained by the condensation of compound 20 with morpholine and 1,2,3,4-tetrahydroquinoline respectively .
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