4-metalated condensed pyrimidines:: Their preparation and reaction with aldehydes under Barbier-type conditions

被引：27

作者：

Therkelsen, FD

Rottländer, M

Thorup, N

Pedersen, EB

机构：

[1] Univ So Denmark, Nucl Acid Ctr, Dept Chem, DK-5230 Odense M, Denmark

[2] H Lundbeck & Co AS, Med Chem Res, DK-2500 Copenhagen, Denmark

[3] Tech Univ Denmark, Dept Chem, DK-2800 Lyngby, Denmark

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 12期

关键词：

D O I：

10.1021/ol049432v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The organometallic intermediate obtained from halogen-metal exchanges of 4-iodo-6-phenylthieno[2,3-d]pyrimidine under Barbier-type conditions was reacted with aldehydes to form the corresponding alcohols in moderate yields. The reaction involving an organolithium intermediate proceeded only at low temperature, whereas the reaction involving a magnesium ate intermediate also proceeded at room temperature. A crystal structure confirms that the expected constitutional alcohol isomer is formed, where no migration has taken place. The conditions were also suitable for 9-benzyl-6-iodopurine.

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页码：1991 / 1994

页数：4

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