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4-Methyl-6-phenyl-pyrimidin-2-amine.

ABSTRACT: The title compound, C(11)H(11)N(3), was synthesized as part of our research into functionalized pyrimidines. It crystallizes with two independent mol-ecules in the asymmetric unit that differ only in the twist between the two aromatic rings; the torsion angles between the rings are 29.9 (2) and 45.1 (2)°. The crystal packing is dominated by inter-molecular N-H⋯N hydrogen bonds between independent and equivalent mol-ecules, forming an infinite three-dimensional network.

SUBMITTER: Li ZJ

PROVIDER: S-EPMC2960917 | biostudies-literature |

REPOSITORIES: biostudies-literature

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N-Butyl-4-methyl-6-phenyl-pyrimidin-2-amine.

Project description:In the title compound, C(15)H(19)N(3), the pyrimidine ring is approximately planar [maximum deviation = 0.007?(1)?Å] and forms a dihedral angle of 3.15?(6)° with the benzene ring. In the crystal packing, inter-molecular N-H?N hydrogen bonds link pairs of neighbouring mol-ecules into dimers with R(2) (2)(8) ring motifs. These dimers are stacked along the b axis.

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Project description:In the title compound, C(18)H(17)N(3), the dihedral angles between the central pyrimidine ring and its directly-bonded and N-bonded pendant phenyl rings are 25.48?(6) and 80.33?(6)°, respectively. The dihedral angle between the phenyl rings is 79.66?(6)°. In the crystal, inversion dimers linked by pairs of N-H?N hydrogen bonds generate R(2) (2)(8) loops. The crystal structure also features weak ?-? [centroid-centroid separation = 3.6720?(7)?Å] and C-H?? inter-actions.

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5-[(4-Fluoro-anilino)meth-yl]-6-methyl-N-(4-methyl-phen-yl)-2-phenyl-pyrimidin-4-amine.

Project description:In the title compound, C(25)H(23)FN(4), the pyrimidine ring makes dihedral angles of 11.3?(2), 24.5?(2) and 70.1?(2)° with the phenyl and two benzene rings, and the mol-ecular conformation is stabilized by an intra-molecular N-H?N hydrogen bond with an S(6) ring motif. In the crystal, a pair of weak C-H?F hydrogen bonds link two mol-ecules into an inversion dimer with an R(2) (2)(16) motif. In the dimer, there is also an inter-molecular ?-? stacking inter-action [centroid-centroid distance = 3.708?(4)?Å] between the fluorinated benzene rings. The dimers are further linked by a C-H?? inter-action, so forming a column along the c axis.

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6-Chloro-N-methyl-5-nitro-N-phenyl-pyrimidin-4-amine.

Project description:In the title compound, C(11)H(9)ClN(4)O(2), the dihedral angle between the aromatic rings is 79.67?(8)°. ?-? stacking between centrosymmetrically related pairs of pyrimidine rings occurs along [100] [centroid-centroid separations = 3.4572?(8) and 3.5433?(7)?Å].

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N-(3-Methyl-phen-yl)pyrimidin-2-amine.

Project description:Two independent mol-ecules comprise the asymmetric unit in the title compound, C(11)H(11)N(3). These differ in terms of the relative orientations of the aromatic rings: the first is somewhat twisted, while the second is approximately planar [dihedral angles between the pyrimidine and phenyl rings = 39.00 (8) and 4.59 (11)°]. The mol-ecules also form distinct patterns in their hydrogen bonding. The first independent mol-ecule forms centrosymmetric dimers featuring an eight-membered {HNCN}(2) synthon. The second independent mol-ecule forms an N-H⋯N hydrogen bond with the other pyrimidine N atom of the first mol-ecule. Thereby, tetra-meric aggregates are formed. These associate via C-H⋯N and C-H⋯π inter-actions, consolidating the crystal packing.

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4-Methyl-6-(piperidin-1-yl)pyrimidin-2-amine.

Project description:The title compound, C(10)H(16)N(4), crystalizes with two mol-ecules (A and B) in the asymmetric unit in which the dihedral angles between the piperidine and pyrimidine rings are 47.5?(1) and 10.3?(1)°. The four C atoms of the pyrimidine ring in one of the mol-ecules are disordered over two sets of sites with occupancy factors 0.508?(11):0.492?(11). In the crystal, the A mol-ecules are linked to one another through N-H?N hydrogen bonds, generating R(2) (2)(8) ring patterns and forming inversion dimers. These dimers are further connected on either side to a B molecule through pairs of N-H?N hydrogen bonds, resulting in a tetra-meric unit.

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5-[(4-Eth-oxy-anilino)meth-yl]-N-(2-fluoro-phen-yl)-6-methyl-2-phenyl-pyrimidin-4-amine.

Project description:The asymmetric unit of the title compound, C(26)H(25)FN(4)O, consists of two symmetry-independent mol-ecules, denoted A and B. The conformation of each mol-ecule is mainly determined by an intra-molecular N-H?N hydrogen bond, which closes a six-membered ring. The dihedral angles between the pyrimidine ring and the phenyl, fluorophenyl and ethoxyphenyl rings are 15.4?(2), 28.4?(2) and 77.5?(2)°, respectively, in mol-ecule A, and 15.9?(2), 2.7?(2) and 61.8?(2)° in mol-ecule B. Inter-molecular N-H?N hydrogen bonds and ?-? stacking inter-actions between pyrimidine rings [centroid-centroid distance = 3.692?(4)?Å] connect mol-ecules A and B into dimers and C-H?O hydrogen bonds link the dimers into zigzag chains along [011]. The (4-eth-oxy-anilino)methyl group of the B mol-ecule is disordered over two sets of sites, the occupancy factor for the major component being 0.900?(2).

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5-Bromo-N-methyl-pyrimidin-2-amine.

Project description:In the title mol-ecule, C(5)H(6)BrN(3), the pyrimidine ring is essentially planar, with an r.m.s. deviation of 0.007?Å. The Br and N atoms substituted to the pyrimidine ring are coplanar with the ring [displacements = 0.032?(1) and 0.009?(5)?Å, respectively], while the methyl C atom lies 0.100?(15)?Å from this plane with a dihedral angle between the pyrimidine ring and the methyl-amine group of 4.5?(3)°. In the crystal, C-H?N, C-H?Br and N-H?N hydrogen bonds link the mol-ecules into a two-dimensional network in the (011) plane.

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2-Chloro-6-methyl-pyrimidin-4-amine.

Project description:In the crystal structure of the title compound, C5H6ClN3, mol-ecules are linked by pairs of N-H?N hydrogen bonds, forming inversion dimers. These dimers are linked via N-H?N hydrogen bonds, forming a two-dimensional network lying parallel to (100). Inversion-related mol-ecules are also linked via a slipped ?-? inter-action, with a centroid-centroid distance of 3.5259?(11)?Å, a normal separation of 3.4365?(7)?Å and a slippage of 0.789?Å.

| S-EPMC3589031 | biostudies-other

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