Volume 20, Issue 2
Heterocyclic Compounds
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ChemInform Abstract: Syntheses of 5-Alkenylpyrimidines by Organotin Reactions.

J. SANDOSHAM

J. SANDOSHAM

Dep. Chem., Univ. Oslo, N-0315 Oslo 3, Norway

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T. BENNECHE

T. BENNECHE

Dep. Chem., Univ. Oslo, N-0315 Oslo 3, Norway

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B. S. MOELLER

B. S. MOELLER

Dep. Chem., Univ. Oslo, N-0315 Oslo 3, Norway

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K. UNDHEIM

K. UNDHEIM

Dep. Chem., Univ. Oslo, N-0315 Oslo 3, Norway

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First published: January 10, 1989

Abstract

The stannylpyrimidine (III), obtainable from the bromide (I) by lithiation and quenching with the stannyl chloride (II), reacts with the vinyl bromides (IV) to give 5-substituted derivatives (V).

ChemInform Abstract

The stannylpyrimidine (III), obtainable from the bromide (I) by lithiation and quenching with the stannyl chloride (II), reacts with the vinyl bromides (IV) to give 5-substituted derivatives (V). The dimer (VI) is obtained in addition to (Va) and (Vc). The preparation of (V) is also possible by condensation of the bromide (Ia) with the respective vinyltin derivatives, e.g. (VII) (→ (Va)). Alternatively, the 5-vinylpyrimidines, e.g. (Va) or (XIII), are accessible from the compound (IX) by a dehydrohalogenation reaction with CsF or from the compound (XI) by a modified Wittig reaction.

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