Preparation of aminopyrimidine compounds

Organic compounds -- part of the class 532-570 series – Organic compounds – Nitrogen attached directly or indirectly to the purine ring...

Reexamination Certificate

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C544S316000, C544S330000

Reexamination Certificate

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10483430

ABSTRACT:
A 2-(N-methyl-N-methanesulfonylamino)pyrimidine compound of the formula (3): [R is a hydrocarbyl group], is prepared by the steps of: (I) reacting an isobutyrylacetate ester with 4-fluorobenzaldehyde and urea in the presence of a protonic compound and a metal salt; (II) oxidizing the reaction product of the step (I); (III) reacting the oxidation product of the step (II) with an organic sulfonyl halide or an organic sulfonyl anhydride; and (IV) reacting the reaction product of the step (III) with N-methyl-N-methanesulfonamide.

REFERENCES:
patent: 5681957 (1997-10-01), Wolters et al.
patent: 6278001 (2001-08-01), Solladie et al.
patent: 6784171 (2004-08-01), Taylor et al.
patent: 6844437 (2005-01-01), Taylor et al.
patent: 6870059 (2005-03-01), Kooistra et al.
patent: 0742212 (1996-11-01), None
patent: 1193259 (2002-04-01), None
patent: 5-178841 (1993-07-01), None
patent: 6-256318 (1994-09-01), None
patent: 90/03973 (1990-04-01), None
patent: 92/01675 (1992-06-01), None
patent: WO 93/08823 (1993-05-01), None
patent: 96/14846 (1996-05-01), None
patent: 97/21687 (1997-06-01), None
patent: WO 97/19917 (1997-06-01), None
patent: 99/07695 (1999-02-01), None
patent: 00/49014 (2000-08-01), None
patent: WO 00/49014 (2000-08-01), None
patent: 00/78730 (2000-12-01), None
patent: 01/04100 (2001-01-01), None
patent: 01/60804 (2001-08-01), None
patent: WO 01/72706 (2001-10-01), None
patent: 01/85702 (2001-11-01), None
patent: WO 01/85975 (2001-11-01), None
patent: WO 02/06266 (2002-01-01), None
patent: WO 03/059901 (2003-07-01), None
patent: 03/097614 (2003-11-01), None
patent: WO 03/106447 (2003-12-01), None
patent: WO 2004/014872 (2004-02-01), None
patent: WO 2004/054986 (2004-07-01), None
patent: WO 2004/103977 (2004-12-01), None
patent: WO 2004/108691 (2004-12-01), None
patent: WO 2005/023779 (2005-03-01), None
patent: WO 2005/028450 (2005-03-01), None
patent: WO 2005/042522 (2005-05-01), None
patent: WO 2005/092867 (2005-10-01), None
patent: WO 2006/067456 (2006-06-01), None
Watanabe et al., “Synthesis and Biological Activity of Methanesulfonamide Pyrimidine- andN-Methanesulfonyl Pyrrole-Substituted 3,5-Dihydroxy-6-heptenoates, a Novel Series of HMG-CoA Reductase Inhibitors”, Bioorganic & Medicinal Chemistry, 1997, vol. 5, No. 2, pp. 437-444.
Grohe et al., Synthese und Reaktionen von 2,4-Dichlorpyrimidin-5-carbon-säuereestern, Libigs Ann. Chem., 1973, pp. 1025-1035.
Kaneko et al. “Preparation of optically active 5,6-epoxyhexanoic acid esters as materials for physiologically active substances” Chemical Abstracts+Indexes, American Chemical Society, Columbus, US 118(11):832 (1993).
Menges et al. “Oxidation Degradation of γ-Butyrolactons into 1,3-Diols via a Criegee Rearrangement of Peroxosulfonates. An Enantioselective Synthesis of Compactin Lactone and its Diastereomer” Synlett 12:901-905 (1993).
Presentation given at the 20th International Congress of Heterocyclic Chemistry in Palermo, Aug. 1-5, 2005.
Presentation given at the Gordon Conference on Heterocyclic Compounds, Salve Regina University, Newport, Rhode Island, Jul. 4-9, 2004.
Sakaki et al. “Lipase-catalyzed asymmetric synthesis of 6-(3-chloro-2-hydroxypropyl)-1,3-dioxin-4-ones and their conversion to chiral 5,6-epoxyhexanoates” Tetrahedron: Asymmetry 2(5):343-346 (1991).
Shao et al. “Asymmetric hydrogenation of 3,5-Dioxoesters catalyzed by Ru-binap complex: A short step asymmetric synthesis of 6-substituted 5,6-dihydro-2-pyrones” Tetrahedron 49(10):1997-2010 (1993).
Andrew J. Blacker et al., U.S. Appl. No. 10/275,092, filed Nov. 1, 2002, WO 01/85975, Nov. 15, 2001.
Robert P. Hof, U.S. Appl. No. 10/501,250, filed Jul. 8, 2004, WO 03/059901, Jul. 24, 2003.
Hermanus C. Bakel Van et al., U.S. Appl. No. 10/518,164, filed Jul. 25, 2005, WO 03/106447, Dec. 24, 2003.
John Horbury et al., U.S. Appl. No. 10/524,235, filed Feb. 10, 2005, WO 2004/014872, Feb. 19, 2004.
Lee Newton et al., U.S. Appl. No. 10/537,723, filed Jun. 7, 2005, WO 2004/054986, Jul. 1, 2004.
Jeffrey N. Crabb et al., U.S. Appl. No. 10/558,390, filed Nov. 29, 2005, WO 2004/108691, Dec. 16, 2004.
Rebecca J. Booth et al., U.S. Appl. No. 10/571,254, filed Mar. 9, 2006, WO 2005/023779, Mar. 17, 2005.
Simon N. Black et al., U.S. Appl. No. 10/572,635, filed Mar. 17, 2006, WO 2005/028450, Mar. 31, 2005.
Tetsuo Okada et al., U.S. Appl. No. 10/576,774, filed Apr. 21, 2006, WO 2005/042522, May 12, 2005.
Jacob H. Kooistra et al., U.S. Appl. No. 11/053,090, filed Feb. 7, 2005, WO 02/06266, Jan. 24, 2002.
Andrew J. Blacker et al., U.S. Appl. No. 11/412,047, filed Apr. 27, 2006, WO 01/85975, Nov. 15, 2001.
Hannah et al. “Structural studies on bioactive compounds. Part 29: palladium catalysed arylations and alkynylations of sterically hindered immunomodulatory 2-amino-5-halo-4,6-(disubstituted)pyrimidines” Bioorg Med Chem. 8(4):739-750 (2000).
Hauser et al. “Synthesis of 5-phenyl-4,6-dimethyl-2-pyrimidol and derivatives from the cyclization of urea with 3-phenyl-2,4-pentanedione” Journal of Organic Chemistry 18(5): 588-593 (1953).
Watanabe et al.; Bioorganic & Medicinal Chemistry, vol. 5, No. 2, 1997, pp. 437-444.
Ma et al., “Lanthanide Triflate Catalyzed Biginelli Reaction. One-Pot Synthesis of Dihydropyrimidinones under Solvent-Free Conditions,” Jouranl ofOrganic Chemistry, 2000, 65(12), 3864-3868.

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