229470-22-8Relevant articles and documents
A New and Efficient Synthesis of Pyrrolo[2,3-d]pyrimidine Anticancer Agents: Alimta (LY231514, MTA), Homo-Alimta, TNP-351, and Some Aryl 5-Substituted Pyrrolo[2,3-d]pyrimidines
Taylor, Edward C.,Liu, Bin
, p. 9938 - 9947 (2007/10/03)
Alimta, as well as homo-Alimta, a nonbridged analogue of Alimta, and TNP-351 have been prepared by a new method that involves Michael addition of the appropriate 1-nitroalkene with 2,6-diamino-3H-pyrimidin-4-one or 2,4,6-triaminopyrimidine, followed by a Nef reaction of the resulting primary nitro Michael adduct. Spontaneous intramolecular cyclization of the resulting aldehyde with the pyrimidine 6-amino group yields the corresponding pyrrolo[2,3-d]pyrimidine. A series of previously unknown 5-arylpyrrolo[2,3-d]pyrimidines was prepared by the same methodology from the above pyrimidines and nitrostyrenes. It has been found that the intermediate primary nitro Michael adduct can be prepared in a single step by sonication of a mixture of an arylaldehyde, nitromethane, and the 6-aminopyrimidine in acetic acid containing ammonium acetate.
A simple and concise synthesis of LY231514 (MTA)
Taylor, Edward C.,Liu, Bin
, p. 4023 - 4026 (2007/10/03)
The pyrrolo[2,3-d]pyrimidine anticancer agent LY231514 (MTA, 1) has been prepared utilizing, as a key sequence, Michael condensation of 2,6-diamino- 4(3H)-pyrimidinone (as the donor) with the nitro olefin 8, followed by a Nef reaction that leads to the annulated pyrrole ring of 1.
