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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 13
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Original Articles

Metallation of 2,4-Dialkoxy-5-bromopyrimidine and Formylation with Dimethylformamide: Isolation of 2,6-Dialkoxy-5-dimethylaminopyrimidine-4-carboxaldehyde

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Pages 1939-1943 | Received 25 Mar 2009, Published online: 08 Jun 2010
 

Abstract

Direct metallation of 2,4-dialkoxy-5-bromopyrimidine with lithium diisopropylamide and consequent trapping by dimethylformamide resulted unexpectedly in the formation of 2,6-dialkoxy-5-dimethylaminopyrimidine-4-carboxaldehyde via displacement of bromine by dimethylamine moiety of dimethylformamide.

ACKNOWLEDGMENTS

We are grateful to the Council for Scientific and Industrial Research, New Delhi [No. 01(2215)/08/EMR-II], for financial support of this work. The University Grants Commission, New Delhi, is also thanked for the award of a junior research fellowship to S. M.

Notes

a Condition A: t1 = 10 min, t2 = 1 h, quenched at rt; condition B: t1 = 30 min, t2 = 15 min, quenched at −78 °C; condition C: t1 = 30 min, t2 = 1 h, quenched at −78 °C; condition D: t1 = 2 h, t2 = 2 h, quenched at −78 °C; where t1 is time of addition of DMF after adding starting material and t2 is time of stirring after DMF addition at −78 °C.

b Isolated yield.

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