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Letters in Drug Design and Discovery

Volumn 5, Issue 4, 2008, Pages 277-280

Antimalarial activity of 2,4-diaminopyrimidines

(3) Morgan, R a Haritakul, R J b Keller, P A a

a UNIVERSITY OF WOLLONGONG (Australia)

b NATIONAL SCIENCE AND TECHNOLOGY DEVELOPMENT AGENCY (Thailand)

Author keywords

Antimalarial; Diaminopyrimidine; Structure activity relationship

Indexed keywords

2,4 DIAMINOPYRIMIDINE DERIVATIVE;

ANTIMALARIAL ACTIVITY; ARTICLE; HYDROPHOBICITY; IC 50; NONHUMAN; PLASMODIUM FALCIPARUM; PRIORITY JOURNAL; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION;

EID: 45249098262 PISSN: 15701808 EISSN: None Source Type: Journal
DOI: 10.2174/157018008784619843 Document Type: Article

Times cited : (25)

References (9)

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- A general synthetic procedure for the preparation of 2,4- diaminopyrimidines is outlined here. To a suspension of 2,4-dichloro-6- methylpyrimidine (2.01 g, 12.3 mmol) in distilled water (50 ml) was added 2,4,6-trimethylaniline (1.8 ml, 17.3 mmol) and the resulting mixture was heated at reflux for 72 hours. The cooled reaction mixture was extracted with DCM (4 x 30 ml, the combined organic layers dried (MgSO4) and concentrated in vacuo. The crude residue was subjected to gravity silica column chromatography and elution with 5% ethyl acetate:hexane gave 2-chloro-6-methyl-4-(2,4,6-trimethylanilino)pyrimidine 4 (1.14 g, 4.4 mmol, 35, as a white powder, mp. 208 °C. MS (CI, m/z 264 (32, M+H 37Cl, 262 (100, M+H 35Cl, 203 (18, 138 (93, HRMS (CI) for C14H17N3 35Cl, calculated 262.1113, found 262.1113; 1H NMR δ 6.98, s, 2H, ArH3′,5′;
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