The desired starting compound 3- N-amino -2, 5, 6- trimethyl thieno[2,3-d]- pyrimidin(3H)–4-one [RJ-1] was prepared from ethyl methyl ketone and ethyl cyano acetate, followed by the treatment of the product with acetic anhydride and hydrazine hydrate. RJ-1 was then treated with various substituted aryl aldehydes to get a new series of Schiff base analogs [RJ-1 a-m] as title compounds. The new compounds were characterized by MP, TLC and representative compounds by 1HNMR, IR, and Mass spectral data. The new title compounds were screened for antibacterial and antifungal activity by using Ampicillin and Miconazole nitrate as standards respectively. It was observed that compounds titled RJ-1d, RJ-1j, RJ-1f and RJ-1l showed good activity. Compounds…show more content… The melting points of the intermediates and products were determined in open capillary tubes and uncorrected. TLC was carried out using silica gel G with solvents as Benzene: Chloroform (1:1) to find the purity of synthesized compounds. The physical data of the compounds are shown table-1. 1HNMR spectra were recorded in CDCl3 using tetra methyl silane (TMS) as internal standard on Bruker AMX. IR spectra of the compounds were recorded using KBr pellet on Shimadzu FTIR-8700 spectrophotometer and frequencies were recorded in wave numbers.
Procedure for the synthesis of 2-Amino-3- carbethoxy-4,5- dimethyl thiophene [S-1]
To a mixture of the ethyl methyl ketone ( 2.88g ;0.04 mol ) , ethyl cyanoacetate(4.52g; 0.04 mol ) and sulphur powder(1.28 g ; 0.04 mol) in ethanol (40 ml), diethyl amine (4.0 ml) was added dropwise with stirring. The mixture was stirred further for 1hr at 45-50OC, chilled overnight and the solid obtained was filtered, washed and recrystallised from ethanol . Yield 46.87%, M.P 84oC, Rf value 0.6 [Solvent system- Benzene: Chloroform (1:1)]
Procedure for the Synthesis of 2-Acetamido-3- carbethoxy-4,5- dimethyl thiophene [ S-1a…show more content… Dai Y, Guo Y, Frey RR, Thienopyrimidine ureas as novel and potent multi- targeted receptor tyrosine kinase inhibitors. J.Med. Chem 2005; 48(19): 6066-83.
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