326855-11-2Relevant articles and documents
Novel procedure for selective C-nitrosation of aminopyrimidine derivatives under neutral conditions. Scope and synthetic applications
Marchal, Antonio,Melguizo, Manuel,Nogueras, Manuel,Sánchez, Adolfo,Low, John N.
, p. 255 - 258 (2002)
A novel simple method, based on treatment with isoamyl nitrite (IAN) in DMSO without any added acid, to produce selective C(5)-nitrosation of aminopyrimidine derivatives is described. It proved to be suitable for a multigram scale and applicable to a larger range of pyrimidine derivatives, including amino-dialkoxypyrimidines, than the procedures previously known. Its scope is analyzed and some example on the usefulness of the newly prepared substances as intermediates in the synthesis of fused heterobicyclic derivatives of potential biological interest is presented.
A concise synthesis of a highly substituted 6-(1H-benzimidazol-1-yl)-5-nitrosopyrimidin-2- amine: Synthetic sequence and the molecular and supramolecular structures of one product and two intermediates
Cobo, Justo,Vicentes, Daniel E.,Rodríguez, Ricaurte,Marchal, Antonio,Glidewell, Christopher
, p. 696 - 702 (2018)
A concise and efficient synthesis of 6-benzimidazolyl-5-nitrosopyrimidines has been developed using Schiff base-type intermediates derived from N4-(2-aminophenyl)-6-methoxy-5-nitrosopyrimidine-2,4-diamine. 6-Methoxy-N4-{2-[(4-methylbenzylidene)amino]phenyl}-5-nitrosopyrimidine-2,4-diamine, (I), and N4-{2-[(ethoxymethylidene)amino]phenyl}-6-methoxy-5-nitrosopyrimidine-2,4-diamine, (III), both crystallize from dimethyl sulfoxide solution as the 1:1 solvates C19H18N6O2·C2H6OS, (Ia), and C14H16N6O3·C2H6OS, (IIIa), respectively. The interatomic distances in these intermediates indicate significant electronic polarization within the substituted pyrimidine system. In each of (Ia) and (IIIa), intermolecular N-H…O hydrogen bonds generate centrosymmetric four-molecule aggregates. Oxidative ring closure of intermediate (I), effected using ammonium hexanitratocerate(IV), produced 4-methoxy-6-[2-(4-methylphenyl-1H-benzimidazol-1-yl]-5-nitrosopyrimidin-2-amine, C19H16N6O2, (II) [Cobo et al. (2018). Private communication (CCDC 1830889). CCDC, Cambridge, England], where the extent of electronic polarization is much less than in (Ia) and (IIIa). A combination of N–H…N and C–H…O hydrogen bonds links the molecules of (II) into complex sheets.
HAIR COLOURANTS COMPRISING TETRAAMINOPYRIMIDINE DERIVATES
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Paragraph 0217; 0218; 0219; 0220, (2017/11/29)
The present disclosure relates to compositions for colouring keratin fibres, in particular human hair, where the composition comprises, in a cosmetic carrier, at least one neutral tetraaminopyrimidine derivate of the general formula (I), (I) in which R1, R2 independently of one another are a group of the formulae (II), (III) or (IV) —(CH2)n— (II) —(CH2)m—O—(CH2)p— (III) —(CH2)m—N(R3)-(CH2)p— (IV) n is 2, 3, 4, 5 or 6, m, p in each case independently of one another are 1, 2 or 3, Y is —OH, —NH2 or —NH-alkyl, R3 is a hydrogen atom, a C1-C6-alkyl group or is a C2-C6-alkenyl group.
MEANS FOR OXIDATIVE DYEING OF KERATIN FIBERS CONTAINING NOVEL TETRA-SUBSTITUTED DERIVATIVES OF PYRIMIDINE
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Paragraph 0263-0267, (2016/10/31)
Agents for oxidatively dyeing keratinous fibers include, in a cosmetic carrier, as an oxidation dye precursor of the developer type, at least one compound of formula (I) as set forth herein, in which R1, R2 can stand independently of each other, for a hydrogen atom, different substituted alkyl groups, and/or different substituted acrylic groups, and Y stands for a hydroxyl group, an amino group, or a C1-C6 alkylamino group, with the proviso that at least one of the moieties from the group R1 and R2 does not stand for a hydrogen atom, and/or the physiologically compatible salt thereof.
Alkoxy-5-nitrosopyrimidines: Useful building block for the generation of biologically active compounds
Marchal, Antonio,Nogueras, Manuel,Sanchez, Adolfo,Low, John N.,Naesens, Lieve,De Clercq, Erik,Melguizo, Manuel
experimental part, p. 3823 - 3830 (2010/10/04)
Several alkoxy-5-nitrosopyrimidines were synthesised and high regioselective and sequential nucleophilic aromatic substitution of methoxy groups in 2-am:ino-4,6-d.imetho;xy-5nitrosopyrimidine was observed. The approach was applied to the synthesis of valu
