- Consecutive SNH and Suzuki-Miyaura cross-coupling reactions-an efficient synthetic strategy to pyrimidines bearing pyrrole and indole fragments
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The combination of the Suzuki-Miyaura cross-coupling and nucleophilic aromatic substitution of hydrogen reactions is a versatile tool for the syntheses of 4-(1R-pyrrol-2-yl)-and 4-(1R-indol-3-yl)-5-(hetero)aryl-substituted pyrimidines from commercially available 5-bromopyrimidine. The S NH [AE, (addition-elimination)] and SN H [AO, (addition-oxidation)] reactions of 5-bromopyrimidine with pyrroles and indoles were studied by gas chromatography-mass spectrometry. The structures of the intermediate σH adducts as well as the pyrrole-(hetero)arylpyrimidine and indole-(hetero)arylpyrimidine dyads were established for the first time by X-ray crystal structure analysis.
- Verbitskiy, Egor V.,Rusinov, Gennady L.,Charushin, Valery N.,Chupakhin, Oleg N.,Cheprakova, Ekaterina M.,Slepukhin, Pavel A.,Pervova, Marina G.,Ezhikova, Marina A.,Kodess, Mikhail I.
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supporting information
p. 6612 - 6621
(2013/01/15)
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- Preparation of head-to-tail φ-conjugated poly(thiophenepyridine) and polypyrimidine by organometallic polycondensation
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The metalation of BrThPyBr (Th: thiophene-2,5-diyl; Py: pyridine-2,5-diyl) and 2-iodo-5-bromopyrimidine with i-PrMgCl proceeds regioselectively. The cross-coupling polycondensation of regioselectively metalated intermediates gives head-to-tail φ-conjugated poly(thiophenepyridine) and polypyrimidine, respectively, and their packing structures in the solid state and optical data are discussed.
- Fukumoto, Hiroki,Fujiwara, Yoshiki,Yamamoto, Takakazu
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scheme or table
p. 992 - 994
(2011/12/05)
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- Pyrimidine compounds
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Pyrimidine derivatives of formula (I) wherein: Q1 and Q2 are independently selected from aryl or carbon linked heteroaryl optionally substituted as defined within; and one of Q1 and Q2 or both Q1 and Q2 is substituted on a ring carbon by one group selected from sulphamoyl, N—(C1-4alkyl)sulphamoyl (optionally substituted by halo or hydroxy), N,N-di-(C1-4alkyl)sulphamoyl (optionally substituted by halo or hydroxy), C1-4alkylsulphonyl (optionally substituted by halo or hydroxy) or a substituent of the formula (Ia) or (Ia′): wherein Q1, Q2, G, R1, Y, Z, Q3, n and m are as defined within; and pharmaceutically acceptable salts and in vivo hydrolysable esters thereof are described. Processes for their manufacture, pharmaceutical compositions and their use as cyclin-dependent serine/threonine kinase (CDK) inhibitors are also described.
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- Pyrimidines From Furfural. A Convenient Synthesis of 5-Bromo- and 5-Chloropyrimidine
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A new method for the preparation of 5-bromo- and 5-chloropyrimidine from furfural has been described.
- Kress, Thomas J.,Szymanski, Edward
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p. 1721 - 1722
(2007/10/02)
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- Process for preparing 5-halopyrimidines
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The reaction of formamide at high temperature with a 4-halo-5-hydroxy-2(5H)-furanone provides high yields of 5-chloro or 5-bromopyrimidines.
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- Process for bromination of pyrimidine
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The process for brominating pyrimidine which comprises reacting bromine at an elevated temperature with the hydrogen halide addition salt of pyrimidine in an organic solvent substantially inert to the action of bromine under the conditions of the process. The process is also shown to be applicable to other nitrogen-containing heterocycles.
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