N-(2-Meth­oxy­benz­yl)-9-(oxolan-2-yl)-9H-purin-6-amine

Zdeněk Trávníček; Igor Popa; Zdeněk Dvořák; Pavel Štarha

doi:10.1107/S1600536813007721

. 2013 Mar 23;69(Pt 4):o588. doi: 10.1107/S1600536813007721

N-(2-Methoxybenzyl)-9-(oxolan-2-yl)-9H-purin-6-amine

Zdeněk Trávníček ^a,^*, Igor Popa ^a, Zdeněk Dvořák ^b, Pavel Štarha ^a

PMCID: PMC3629632 PMID: 23634119

Abstract

The title compound, C₁₇H₁₉N₅O₂, features an almost planar purine skeleton (r.m.s. deviation = 0.009 Å) substituted by a tetrahydrofuran ring, which adopts an envelope conformation. The purine and benzene rings subtend a dihedral angle of 66.70 (3)°. In the crystal, pairs of N—H⋯N hydrogen bonds connect adjacent molecules into inversion dimers. C—H⋯N, C—H⋯O, C—H⋯π and π–π interactions [pyrimidine ring centroid–centroid distance = 3.3909 (1) Å] connect the dimers into a three-dimensional architecture.

Related literature

For an alternative synthetic procedure and the biological activity of benzyl-substituted 6-benzylamino-9-tetrahydropyran-2-yl-9H-purine derivatives, see: Szüčová et al. (2009 ▶). For a related structure, see: Štarha et al. (2013 ▶).

Experimental

Crystal data

C₁₇H₁₉N₅O₂
M _r = 325.37
Monoclinic,
a = 8.87210 (19) Å
b = 8.37534 (17) Å
c = 20.7445 (4) Å
β = 90.4360 (19)°
V = 1541.42 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 110 K
0.35 × 0.30 × 0.30 mm

Data collection

Agilent Xcalibur Sapphire2 diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T _min = 0.967, T _max = 0.972
12687 measured reflections
2719 independent reflections
2415 reflections with I > 2σ(I)
R _int = 0.014

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.087
S = 1.04
2719 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2011 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Click here for additional data file.^{(18.2KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813007721/ng5319sup1.cif

e-69-0o588-sup1.cif^{(18.2KB, cif)}

Click here for additional data file.^{(133.5KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813007721/ng5319Isup2.hkl

e-69-0o588-Isup2.hkl^{(133.5KB, hkl)}

Click here for additional data file.^{(6.5KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813007721/ng5319Isup3.cml

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

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

Cg is the centroid of the C10–C15 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N6—H6⋯N7ⁱ	0.88	2.32	3.145 (2)	157
C8—H8⋯Cg ⁱ	0.95	2.86	3.6214 (14)	138
C12—H12⋯O2ⁱⁱ	0.95	2.60	3.459 (2)	150
C13—H13⋯N3ⁱⁱ	0.95	2.55	3.489 (2)	170

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

This work was supported by Palacký University (grant No. PrF_2013_015). The authors wish to thank Mr Tomáš Šilha for performing the CHN elemental analysis.

supplementary crystallographic information

Comment

The molecule of N-(2-methoxybenzyl)-9-(oxolan-2-yl)-9H-purin-6-amine consists of six-membered pyrimidine and five-membered imidazole rings merged to the essentially planar purine skeleton, which is substituted by 2-methoxybenzylamine and oxolan-2-yl at the C6, and N9 position, respectively (Figure 1). Two N6—H6···N7 hydrogen bonds (Table 1) connect the molecules into the centrosymmetric dimers (Figure 2) with coplanar purine moieties (dihedral angle of 0.00 (3)°). Except for the hydrogen bonds, the C—H···N, C—H···O, C—H···π and π–π interactions (Figure 2) also link the individual molecules within the crystal structure into a three-dimensional architecture. The planar pyrimidine (the most deviated atoms from the LSQ-plane fitted through its atoms: C5, 0.0122 (13) Å) and imidazole (the most deviated atom from the LSQ-plane fitted through its atoms: C8, -0.002 (2) Å) rings of the purine moiety form the dihedral angle of 0.72 (4)°. The planes fitted through the atoms of the purine and benzene rings form the dihedral angle of 66.70 (3)°.

Experimental

N-(2-methoxybenzyl)-9-(oxolan-2-yl)-9H-purin-6-amine, a perspective ligand of the transition metal complexes, was synthesized by a modification of the recently reported method (Szüčová et al., 2009). 6-Chloropurine reacted with 2,3-dihydrofurane in a molar ratio of 1:2 for 15 min at laboratory temperature in a minimum volume of ethanol, followed by the addition of CF₃COOH (1.30 molar equivalent of 6-chloropurine). The mixture was stirred at laboratory temperature for 24 h and after that it was neutralized by 10% NH₄OH, evaporated to dryness, washed by distilled water, methanol and diethyl ether and dried in desiccator over P₄O₁₀. The obtained intermediate, i.e. 6-chloro-9-(oxolan-2-yl)-9H-purine interacted with 2-methoxybenzylamine and triethylamine (molar ratio of 1: 1.33: 1.67, respectively) in N,N`-dimethylformamide (90 °C, 150 min). Again, the solvents were partly evaporated and the obtained product was separated by filtration after it was suspended in distilled water. The title compound was washed with distilled water, methanol and diethyl ether and dried (in a desiccator over P₄O₁₀). Single-crystals were prepared by recrystallization of the product from ethanol. Analysis calculated for C₁₇H₁₉N₅O₂: C 62.8, H 5.9, N 21.5%; found: C 62.6, H 6.1, N 21.2%. Elemental analysis (C, H, N) was performed on a Thermo Scientific Flash 2000 CHNO-S Analyzer.