3-Benzyl-6-butyl-5-propyl-3H-1,2,3-triazolo[4,5-d]pyrimidin-7(6H)-one

Xiao-Hua Zeng; Shou-Heng Deng; Hong-Mei Wang; Ai-Hua Zheng; Ping Chen

doi:10.1107/S1600536810045575

. 2010 Nov 13;66(Pt 12):o3140–o3141. doi: 10.1107/S1600536810045575

3-Benzyl-6-butyl-5-propyl-3H-1,2,3-triazolo[4,5-d]pyrimidin-7(6H)-one

Xiao-Hua Zeng ^a, Shou-Heng Deng ^b, Hong-Mei Wang ^a,^*, Ai-Hua Zheng ^a, Ping Chen ^b

PMCID: PMC3011388 PMID: 21589440

Abstract

In the title compound, C₁₈H₂₃N₅O₂, the triazolopyrimidine ring system is essentially planar, with a maximum displacement of 0.032 (2) Å, and forms a dihedral angle of 87.59 (15)° with the phenyl ring. In the crystal, molecules are linked by intermolecular C—H⋯O hydrogen bonds and C—H⋯π interactions into chains parallel to the c axis.

Related literature

For the biological activity of 8-azaguanine derivatives, see: Roblin et al. (1945 ▶); Ding et al. (2004 ▶); Mitchell et al. (1950 ▶); Levine et al. (1963 ▶); Montgomery et al. (1962 ▶); Yamamoto et al. (1967 ▶); Bariana (1971 ▶); Holland et al. (1975 ▶); Zeng et al. (2010 ▶). For related structures, see: Ferguson et al. (1998 ▶); Li et al. (2004 ▶); Zhao, Xie et al. (2005 ▶); Zhao, Hu et al. (2005 ▶); Zhao, Wang & Ding (2005 ▶); Chen & Shi (2006 ▶); Maldonado et al. (2006 ▶); Xiao & Shi (2007 ▶); Wang et al. (2006 ▶, 2008 ▶); Zeng et al. (2006 ▶, 2009 ▶).

Experimental

Crystal data

C₁₈H₂₃N₅O₂
M _r = 341.41
Orthorhombic,
a = 28.328 (6) Å
b = 14.818 (3) Å
c = 8.7995 (16) Å
V = 3693.7 (12) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.19 × 0.15 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.984, T _max = 0.992
18673 measured reflections
3346 independent reflections
2842 reflections with I > 2σ(I)
R _int = 0.041

Refinement

R[F ² > 2σ(F ²)] = 0.080
wR(F ²) = 0.173
S = 1.21
3346 reflections
228 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1999 ▶) and PLATON (Spek, 2009) ▶; software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810045575/rz2509sup1.cif

e-66-o3140-sup1.cif^{(20.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045575/rz2509Isup2.hkl

e-66-o3140-Isup2.hkl^{(164.2KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 is the centroid of the the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1ⁱ	0.93	2.43	3.259 (4)	148
C15—H15B⋯Cg1ⁱ	0.97	2.94	3.711 (3)	137

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Symmetry code: (i) Inline graphic .

Acknowledgments

We gratefully acknowledge the financial support for this work by the National Basic Research Program of China (2003CB114400), the National Natural Science Foundation of China (20372023, 20102001), the Educational Commission of Hubei Province of China (grant Nos. B200624004, B20092412, B20102103) and the Shiyan Municipal Science and Technology Bureau (grant No. 20061835).

supplementary crystallographic information

Comment

The derivatives of heterocycles containing the 8-azaguanine system, which are well known bioisosteres of guanine, are of great importance because of their remarkable biological properties. Some of these activities include antimicrobial or antifungal activities (Roblin et al., 1945; Ding et al., 2004; Zeng et al., 2010), encephaloma cell inhibitor activity (Mitchell et al., 1950; Levine et al., 1963), antileukemie activity (Montgomery et al., 1962), hypersusceptibility inhibitor activity and acesodyne activity (Yamamoto et al., 1967; Bariana, 1971; Holland et al., 1975).

In recent years, Ding's group has been engaged in the preparation of derivatives of 8-azaguanine via aza-Wittig reaction of β-ethoxycarbonyl iminophosphoranes with aromatic isocyanates (Zhao, Xie et al., 2005). As a continuation of our research for new biologically active heterocycles, the title compound was obtained from β-ethoxycarbonyl iminophosphorane with alphalic isocyanate, and structurally characterized in this context.

In the title compound (Fig. 1), bond lengths and angles within the triazolopyrimidinone system are in good agreement with those observed for closely related structures (Zhao, Hu et al., 2005; Zhao, Wang & Ding, 2005). As reported for related compounds (Ferguson et al., 1998; Li et al., 2004; Maldonado et al., 2006; Zeng et al., 2006, 2009; Wang et al., 2006, 2008; Xiao & Shi, 2007; Chen & Shi, 2006), the triazolopyrimidine ring system is essentially planar, with a maximum displacement of 0.032 (2) Å for atom N4, and forms dihedral angles of 87.59 (15)° with the C1–C6 phenyl ring. In the crystal packing, molecules are linked by intermolecular C—H···O hydrogen bonds and C—H···π interactions (Table 1) into chains parallel to the c axis.

Experimental

To the solution of carbodiimide prepared according to Zeng et al. (2006) in a mixed solvent (CH₂Cl₂/PrOH,1:4 v/v, 15 ml) was added a fresh prepared solution of Na/PrOH (0.1 g/2 ml). After stirring the reaction mixture for 6 h, the solvent was removed under reduced pressure and the residue was recrystallized from EtOH to give the title compound in 75% yield (m. p. 464 K). Elemental analysis: calculated for C₁₄H₁₅N₅O₂: C, 63.32; H, 6.79; N, 20.51%. Found: C, 62.75; H, 6.98; N, 20.22%. Crystals suitable for X-ray diffraction study were obtained by recrystallization from EtOH and dichloromethane (1:3 v/v) at room temperature.