4-Amino-5-(arylaminomethyl)-2-(methylthio)furo[2,3-d]pyrimidines via Mitsunobu Reaction of 4-Amino-5-(hydroxymethyl)-2-(methylthio)furo[2,3-d]pyrimidine with N-Mesyl- and N-Nosylarylamines

Abstract

An efficient method for the synthesis of 4-amino-5-(arylaminomethyl)-2-(methylthio)furo[2,3-d]pyrimidines via the Mitsunobu reaction of 4-amino-5-(hydroxymethyl)-2-(methylthio)furo[2,3-d]pyrimidine with N-mesyl-and N-nosylarylamines, and subsequent removal of the mesyl and nosyl groups, has been developed. The influence of substituents in the arylamine moiety on the Mitsunobu reaction was investigated. An unexpected nucleophilic substitution of a nitro group in the reaction of N-({4-amino-2-(methylsulfonyl)furo[2,3-d]pyrimidin-5-yl}methyl)-4-nitro-Nphenylbenzenesulfonamide with sodium methoxide was observed.

Palladium-Catalyzed Regiocontrolled Domino Synthesis of N-Sulfonyl Dihydrophenanthridines and Dihydrodibenzo[c,e]azepines: Control over the Formation of Biaryl Sultams in the Intramolecular Direct Arylation

“…Under the optimized condition, the sulfonanilides 20 , 21 , and 22 containing an electron-donating or withdrawing group at the 2-position exhibit similar reactivity with 6 affording dihydrophenanthridines 33 – 35 in excellent yields (Table ). While the sulfonanilide 23 containing a substituent at the 4-position sustained similar reactivity with 6 yielding dihydrophenanthridine 36 in 92% yield, compound 24 afforded dihydrophenanthridine 37 in somewhat reduced yield. Interestingly, 3-substituted sulfonanilides 25 and 26 formed only one regioisomer of dihydrophenanthridines 38 and 39 , resulted from intramolecular direct arylation occurred exclusively at the para -position to the concerned group.…”

Application of N-Dodecyl l-Peptide to Enhance Serum Stability while Maintaining Inhibitory Effects on Myometrial Contractions Ex Vivo

“…With the o NBS group installed, sulfonamide resin 5 was treated with di- iso -propyl azodicarboxylate (DIAD), triphenylphosphine and farnesol. N -Farnesyl peptide resin 6 was provided in 55% conversion as demonstrated by LC-MS analysis of material after resin cleavage [50,51,52,53]. The o NBS group was removed by treatment with thiophenol and DBU in DMF [52].…”