Organic Process Research & Development
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(propargylamino)pyrimidine-5-carbonitrile derivatives as pest-control agents for use in
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Kuragano, T.; Tanaka, Y. Preparation of 4-phenyl or heterocyclylpyrimidine
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of pyrimidine derivatives as kinase inhibitors and therapeutic applications thereof.
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heteroaryl and heterocycle compounds as PI3K inhibitors. WO2014015523A1, 2014.
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compounds as PI3K inhibitors and their use. WO2016045591A1, 2016.
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Kloetzer, W.; Herberz, M., Reactions of 4,6-dichloro-5-formylpyrimidine. Monatsh.
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series. XVII. Syntheses and reactions of pyrimidine-5-carboxaldehydes. Justus Liebigs Ann.
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acetylpyrimidines. 4,6-Dihydroxy-5-acetylpyrimidine and preparation of 4',5-bipyrimidines
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and heterocycles. Org. React. (Hoboken, NJ, U. S.) 1997, 49, No pp. given.
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18. Procedure for Table 1: To a solution of hydroxylamine hydrochloride (3 eq.) in the
corresponding solvents, intermediate 5 (3 g, 14.7 mmol) was added in portions at 20-30 C.
And then the resulting reaction mixture was stirred for 15 h.
19.
Bredereck, H.; Simchen, G.; Wagner, H.; Santos, A. A., Syntheses in the heterocyclic
5-Deazariboflavin. JP59005186A, US4567260, 1984.
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Jones, G.; Stanforth, S. P., The Vilsmeier reaction of fully conjugated carbocycles
a
series of 5-
o
Dropping hydroxylamine hydrochloride aqueous solution to a suspension of
intermediate 5 vs. adding intermediate 5 in portions into an aqueous solution of
hydroxylamine hydrochloride.
20.
Procedure for Table 2: To a solution of hydroxylamine hydrochloride in the solvents
of ethanol/water (2 vol./10 vol.), intermediate 5 (6 g, 29.5 mmol) was added in portions at 20-
30 oC. And then the resulting reaction mixture was stirred for 15 h.
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