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Volumn , Issue 13, 2009, Pages 2137-2142

First efficient palladium-catalyzed aminations of pyrimidines, 1,2,4-triazines and tetrazines by original methyl sulfur release

(5) Pellegatti, Laurent a Vedrenne, Emeline a Leger, Jean Michel b Jarry, Christian b Routier, Sylvain a

a UNIVERSITÉ D'ORLÉANS (France)

b Laboratoire de Pharmacochimie (France)

Author keywords

Aminations; Copper; Cross coupling; Palladium; Sulfur

Indexed keywords

1,2,4 TRIAZINE DERIVATIVE; PALLADIUM; PYRIMIDINE DERIVATIVE; SULFUR DERIVATIVE; TETRAZINE DERIVATIVE;

AMINATION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION;

EID: 68949161989 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0029-1217699 Document Type: Article

Times cited : (14)

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- General Procedure for the Heterocyclic Amination: In a sealed microwave vial were successively added the SMe derivative, the amine (1.2 equiv, copper(I) methylsalicylate (2.0 equiv, Cs2CO3 (2.2 equiv, Pd(OAc)2 (10 mol, and xantphos (20 mol, Anhydrous toluene was added and the suspension was subjected to MW irradiation at 170° C for 2 h. The reaction mixture was cooled to r.t. and the solvent was removed under reduced pressure. The crude material was immediately purified by chromatography on silica gel (CH2Cl2) to afford the attempted compound. Compound 2: Rf 0.65 (CH2Cl2-MeOH, 95:5, mp 164-165°C (CH2Cl2, IR (ATR diamond, 3196, 2961, 1595, 1574, 1507, 1447, 1323, 1291, 1107, 1025, 890, 810 cm-1. 1H NMR (250 MHz, CDCl3, δ, 3.82 (s, 3 H, 6.93 (d, J, 9.0 Hz, 2 H, 7.54 (d, J, 9.0 Hz, 2 H, 7.78 br s
- 4O: 203.0933; found: 203.0946.

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- Crystallographic Study: The structure of compound 2 has been established by X-ray crystallography (Figure 1, Colorless single crystals of 2 were obtained by slow evaporation from a methanol-chloroform (20:80) solution. The unit cell dimensions were determined using the leastsquares fit from 25 reflections (25° < c < 35°, a, 5.628 (1) Å, b, 8.211 (5) Å, c, 10.741 (2) Å, α, 101.05 (3)°, β, 84.27 (1)°, γ, 91.47 (3)°. Space group: P-1, Z, 2, μCu, Kα, 0.783 mm-1. 1740 unique reflections were measured; final R, 4.27, all data, Intensities were collected with an Enraf-Nonius CAD-4 diffractometer using the CuKα radiation and a graphite monochromator up to c, 68.91°. The data were corrected for Lorentz and polarization effects and for empirical absorption correction.15 The structure was solved by direct methods Shelx 86 and refined using
- 16,17 An intermolecular hydrogen bond partially contributed to the crystal cohesion. Indeed, the linker N7 (I) acts as a donor to the N1 (II) of the triazine moiety. The distance between N7 (I) and N1 (II), and the N7-H7 (I)⋯N1 (II) angle were found to be 2.978 (2) Å and 168.55°, respectively. Symmetry code of intermolecular hydrogen bond is: I (x, y, z); II (1-x, 1-y, 1-z). CCDC 726564 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.uk/conts/retrieving.html (or from Cambridge Crystallographic Data Centre, University Chemical Lab, 12 Union Road, Cambridge,CB2 1EZ, U.K.; E-mail: deposit@ccdc.cam.ac.uk.).

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