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Ethyl 7-(2-chloro-phen-yl)-5-trifluoro-meth-yl-4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidine-6-carboxyl-ate.

ABSTRACT: In the title compound, C(15)H(12)ClF(3)N(4)O(2), the dihydro-pyrimidine ring exhibits an envelope conformation. The dihedral angle between the mean planes of the dihydro-pyrimidine and phenyl rings is 83.94?(6)°. The OCH(2)CH(3) group is disordered over two sites with occupancies of 0.155?(3) and 0.845?(3). The crystal packing is stabilized by inter-molecular N-H?N hydrogen bonds.

SUBMITTER: Mou J

PROVIDER: S-EPMC2983298 | biostudies-literature | 2010 Sep

REPOSITORIES: biostudies-literature

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Ethyl 7-(2-chloro-phen-yl)-5-trifluoro-meth-yl-4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidine-6-carboxyl-ate.

Mou Jie J Yu Chen-Xia CX Yao Chang-Sheng CS

Acta crystallographica. Section E, Structure reports online 20100925 Pt 10

In the title compound, C(15)H(12)ClF(3)N(4)O(2), the dihydro-pyrimidine ring exhibits an envelope conformation. The dihedral angle between the mean planes of the dihydro-pyrimidine and phenyl rings is 83.94 (6)°. The OCH(2)CH(3) group is disordered over two sites with occupancies of 0.155 (3) and 0.845 (3). The crystal packing is stabilized by inter-molecular N-H⋯N hydrogen bonds. ...[more]

PMID: 21587613

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Ethyl 2-benzyl-sulfanyl-7-(2-chloro-phen-yl)-5-methyl-4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidine-6-carboxyl-ate.

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Ethyl 7-chloro-methyl-5-(2-chloro-phen-yl)-7-hydr-oxy-2-methyl-sulfanyl-4,5,6,7-tetra-hydro-1,2,4-triazolo[1,5-a]pyrimidine-6-carboxyl-ate.

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Project description:This work introduces a new additive named 4,4'-trimethylenedipiperidine for the practical and ecofriendly preparation of ethyl 5-amino-7-(4-phenyl)-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate derivatives. This chemical is commercially available and easy to handle. It also possesses a low melting point and a broad liquid range temperature, high thermal stability, and good solubility in water. Based on green chemistry principles, the reaction was performed in a) a mixture of green solvents i.e. water and ethanol (1:1 v/v) at reflux temperature, and b) the additive was liquefied at 65 °C and the reaction was conducted in the liquid state of the additive. High yields of the desired triazolo-pyrimidines were obtained under both aforementioned conditions. Our results demonstrated that this additive, containing 2 Lewis base sites and able to act as an acceptor-donor hydrogen bonding group, is a novel and efficient alternative to piperidine, owing to its unique properties such as its reduced toxicity, nonflammable nature, nonvolatile state, broad liquid range temperature, high thermal stability, and ability to be safely handled. Furthermore, this additive could be completely recovered and exhibited high recyclability without any change in its chemical structure and no significant reduction in its activity. The current methodology has several advantages: (a) it avoids the use of hazardous materials, as well as toxic, volatile, and flammable solvents, (b) it does not entail tedious processes, harsh conditions, and the multistep preparation of catalysts, (c) it uses a metal-free and noncorrosive catalyst, and (d) reduces the generation of hazardous waste and simple work-up processes. The most important result of this study is that 4,4'-trimethylenedipiperidine can be a promising alternative for toxic, volatile, and flammable base reagents in organic synthesis owing to its unique properties.

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Ethyl 2-isopropyl-amino-6-methyl-8-oxo-3-phenyl-3H,8H-furo[2,3-d][1,2,4]triazolo[1,5-a]pyrimidine-7-carboxyl-ate.

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Project description:There are two crystallographically independent mol-ecules in the asymmetric unit of the title compound, C(21)H(18)N(4)O(4). The substituted benzopyran portion of one of the independent mol-ecules exhibits disorder [occupancy 0.5248?(18):0.4752?(18)], which was modelled by using two sets of atomic positions and restraints on the chemically equivalent bond lengths and angles. The central, partially saturated pyrimidine rings of both independent mol-ecules were found to assume unsymmetrical half-chair conformations. The hy-droxy-phenyl substituent occupies an equatorial position in both mol-ecules, and is rotated by 55.6?(1)° from the mean plane of the pyrimidine ring in one independent mol-ecule, and by 53.4?(1)° in the other. In the crystal, there are two types of inter-molecular hydrogen bond present: reciprocal N-H?N inter-actions join the two crystallographically independent mol-ecules into a dimer and O-H?N inter-actions link the dimers into sheets in the ab plane.

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