Synthesis and biological activity of some 5-substituted 2,4-diamino-6-alkylpyrimidines. 3

Abstract

2,4-Diamino-6-methylpyrimidines having saturated straight-chain alkyl groups (C3, Cs-C8, Ciq) in the 5 position were less potent growth inhibitors (IDS0 1.1 to 53 µ ) of mouse mammary adenocarcinoma cells (TA3) in vitro than 2,4-diamino-5-( 1 -adamantyl)-6-methylpyrimidine (DAMP) (15a) (IDso6.0 M).The IDS0 values for another series of 2,4-diamino-6-methylpyrimidines having increasingly bulky 5 sub-

Hydrogen‐bonded supramolecular polymers as self‐healing hydrogels: Effect of a bulky adamantyl substituent in the ureido‐pyrimidinone monomer

“…Our route to the adamantyl‐substituted pyrimidinone 3 was different from that reported by another group, where the reaction was carried out in the presence of stoichiometric amounts of potassium tert ‐butoxide. Because this procedure required an additional step (evaporation of ethanol under reduced pressure) and considering that the reported yield (41%) was not particularly high, we decided to follow the classic method, notwithstanding the existence of other reports on the alkoxide method . The method we used in this study was reported for the first time in 1886 by Behrend, and employed subsequently with satisfactory yields .…”

Fused pyridothienopyrimidine heterocycles. 2*. A facile and efficient synthesis of the annelated pyrido[3′,2′:4,5]thieno-[2,3-e]pyrimido[3,2-c]pyrimidones

“…Then the reaction mixture was poured into ice water, and the precipitated solid product was collected by filtration, washed with water, dried, and recrystallized from MeOH to afford the corresponding azido compound 2. (4). A solution of iminophosphorane 3 (1.5 g, 3 mmol) in acetic acid (80%, 20 ml)) was heated under reflux for 5 h. The solvent was then removed in vacuum, and the resulting solid product was digested with MeOH, collected by filtration, washed well with MeOH to remove Ph 3 PO, dried, and recrystallized from AcOH to afford compound 4 as white prisms (0.8 g, 89%); mp 287-289ºC (reported, >360°C [17]).…”

“…The pyridothienopyrimidine ring system represents an important class of heterocyclic compounds owing to their medicinal interest [2,3]. In addition, certain pyrimidines and annelated pyrimidine derivatives are known to display anticancer, antimalarial, and antifilarial activitives [4,5]. These features prompted us to design a specific program aimed at constructing novel tetracyclic ring systems containing a pyrimidine moiety, which condensed with pyridothienopyrimidine derivatives.…”

4-Hydroxy-6-(4-methoxyphenyl)-4-phenyl-1,3-diazinane-2-thione

“…For general background to pyrimidines, see: Cheng (1969); Scott et al (1959); Jonak et al (1972); Falco et al (1961); Ram (1990); Howells et al (1981); Pershin et al (1972); Matolcsy (1971); Prikazchikova et al (1975). For the synthesis, see: Paghdar et al (2007).…”