134373-07-2Relevant academic research and scientific papers
A one-step ring transformation/ring annulation approach to pyrrolo[2,3-d]pyrimidines. A new synthesis of the potent DHFR inhibitor TNP-351
Taylor,Patel,Jun
, p. 6684 - 6687 (2007/10/03)
Condensation of amidines with 2-amino-3-cyanofurans gives 2-substituted-4-aminopyrrolo[2,3-d]pyrimidines by a ring-opening, ring-recyclization sequence of reactions through which the starting furan 2-amino nitrogen becomes the pyrrole nitrogen of the final product and one of the amidine nitrogens becomes N-1 of the fused pyrimidine ring. 2,4-Diamino-5-[2-(4-carbethoxyphenyl)ethyl]pyrrolo[2,3-d]pyrimidine, a key intermediate in the synthesis of the DHFR inhibitor TNP-351, has been prepared in one step by reaction of ethyl 4-[2-(2-amino-3-cyanofuran-4-yl)ethyl]benzoate with guanidine.
A Novel Synthetic Approach to Pyrrolopyrimidine Antifolates
Miwa, Tetsuo,Hitaka, Takenori,Akimoto, Hiroshi
, p. 1696 - 1701 (2007/10/02)
A novel and efficient synthetic method for the synthesis of pyrrolopyrimidine antifolates is described.The key reaction of this method is the photo-initiated free radical addition of bromomalononitrile or ethyl bromocyanoacetate to an enol ether to afford the backbone skeleton of the targeted antifolate molecule.The key intermediates 3 or 4 are smoothly converted to the pyrrolopyrimidine antifolates 1 or 2 in three steps and in high overall yield.
