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

Journal of Organic Chemistry

Volumn 68, Issue 26, 2003, Pages 9938-9947

  Taylor, Edward C ^a   Liu, Bin ^a,b  

^a PRINCETON UNIVERSITY   (United States)

^b ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; ADDITION REACTIONS; ALDEHYDES; AMINO ACIDS; METHANE; STYRENE; SUBSTITUTION REACTIONS; TUMORS;

ANTICANCER AGENTS;

SYNTHESIS (CHEMICAL);

2,4,6 TRIAMINOPYRIMIDINE; 2,6 DIAMINO 3H PYRIMIDIN 4 ONE; 6 AMINOPYRIMIDINE; ACETIC ACID; ALDEHYDE; AMMONIUM ACETATE; ANTINEOPLASTIC AGENT; HOMO ALIMTA; LOMETREXOL; N [4 (2 AMINO 4 OXO 4,7 DIHYDRO 3H PYRROLO[2,3 D]PYRIMIDIN 5 YL)BENZOYL]GLUTAMIC ACID; N [4 [3 (2,4 DIAMINO 7H PYRROLO[2,3 D]PYRIMIDIN 5 YL)PROPYL]BENZOYL]GLUTAMIC ACID; NITROALKANE; NITROMETHANE; NITROSTYRENE; PEMETREXED; PYRIMIDINE DERIVATIVE; PYRROLO[2,3 D]PYRIMIDINE DERIVATIVE; STYRENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CYCLIZATION; DRUG SYNTHESIS; MASS SPECTROMETRY; MICHAEL ADDITION; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SAPONIFICATION;

ANTINEOPLASTIC AGENTS; GLUTAMATES; GUANINE; METHOTREXATE; MOLECULAR STRUCTURE; PYRIMIDINES; PYRROLES;

EID: 0346363141     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo030248h     Document Type: Article

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51. This is the same general strategy for formation of the annulated pyrrole ring that was utilized by Miwa and co-workers for the synthesis of TNP-351 (4) and 1 (ref 11) and by us in our initial synthesis of 1 (ref 1).