Thieno[2,3‐d]pyrimidines. I. A new method for the preparation of esters and amides of thieno[2,3‐d] pyrimidine‐6‐carboxylic acids

doi:10.1002/JHET.5570080315

Paper

Thieno[2,3‐d]pyrimidines. I. A new method for the preparation of esters and amides of thieno[2,3‐d] pyrimidine‐6‐carboxylic acids

Published Jun 1, 1971 · A. A. Santilli, D. H. Kim, S. Wanser

Journal of Heterocyclic Chemistry

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51

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Abstract

A novel method for the preparation of esters and amides of thieno[2,3-d]pyrimidine-6-carb-oxylic acids was described. A typical example was the direct formation of ethyl 5-amino-2-methylthiothieno[2,3-d]pyrimidine-6-earboxylate(IIIa) from 4-chloro-2-methylthio-5-pyrimidine-carbonitrile (Ia) and ethyl mercaptoacetate in refluxing ethanol containing sodium carbonate. Displacement of the methylthio group in IIIa by various amines gave the corresponding amino derivatives. The reactions of IIIa and related compounds with acetylating agents such as acetic anhydride or chloroacetyl chloride gave various products. Treatment of 5-carbethoxy-4-chloro-2-phenylpyrimidine(IV) with methyl mercaptoacetate afforded the dechloro intermediate diester Va, which cyclized on reaction with sodium ethoxide to form methyl 5-hydroxy-2-phenylthieno-[2,3-d]pyrimidine-6-carboxylate (Vla). The synthesis was expanded to include the preparation of various new 2,4,5-trisubstituted thieno[2,3-d]pyrimidine-6-carboxylic acid esters and amides (Charts I-V).

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This novel method allows for the preparation of esters and amides of thieno[2,3-d]pyrimidine-6-carboxylic acids, with potential applications in the synthesis of new 2,4,5-trisubstituted compounds.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Thieno[2,3‐d]pyrimidines. I. A new method for the preparation of esters and amides of thieno[2,3‐d] pyrimidine‐6‐carboxylic acids

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References

Pyrrolo[2,3-d] pyrimidines. I. 5-hydroxypyrrolo[2,3-d] pyrimidines

5-Hydroxy-7-alkyl-2-phenyl-7H-pyrrolo[2,3-d]pyrimidine-6-carbonitriles and 5-hydroxy-2-phenyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid, e

Reaktionen des 4,6-Dichlor-5-formylpyrimidins

Methanolysis of 4.6-dichloro-5-formylpyrimidine (I) produces 4,6-dimethoxy-5-formylpyrimidine (III), while dimethylacetal of I yields 4,6-dimethoxy-5-formylpyrimidine (III).

Heilmittelchemische Studien in der heterocyclischen Reihe. 26. Mitteilung

The synthesized compounds show diuretic, cardiac, and tumor-inhibiting properties, with some showing diuretic and cardiac activity and others inhibiting tumor growth.

Citations

2‐Amino‐4‐arylthiophene‐3‐carbonitrile and formamidine acetate as key building units for the synthesis of 5‐arylthieno[2,3‐d]pyrimidin‐4‐amines

This study developed a novel method for synthesizing 5arylthieno[2,3d]pyrimidin4amine analogues using a three-step reaction, utilizing 2aminothiophenes, Gewald method, and formamidine acetate.

Synthesis, Antimicrobial, and Anticancer Activities of a New Series of Thieno[2,3-d] Pyrimidine Derivatives

A new series of thieno[2,3-d] pyrimidine derivatives has been synthesized, showing strong antimicrobial and anticancer activities.

Vilsmeier–Haack formylation of ethyl [(4,6-dihydroxypyrimidin-2-yl)sulfanyl]acetate

The Vilsmeier-Haack formylation of ethyl [(4,6-dihydroxypyrimidin-2-yl)sulfanyl]acetate can produce various compounds, with varying degrees of substitution of hydroxy groups in the pyrimidine ring.

Synthesis of novel peri-fused heterocyclic systems—pyrimido[4,5,6-de][1,8]naphthyridines, based on interaction of 4,6-dichloro-2-methylthiopyrimidine-5-carbaldehyde with geminal enediamines

The synthetic approach to novel peri-fused heterocyclic systems, pyrimido[4,5,6-de][1,8]naphthyridines, involves treating 4,6-dichloro-2-methylthiopyrimidine-5-carbaldehyde with geminal ened

Synthesis of novel pyrazolo[3,4‐d]pyrimidines peri‐fused with 1,4‐diazepine, 1,4‐thiazepine, and 1,2,4‐triazepine rings

This study presents a simple and efficient synthesis of novel ortho- and peri-annulated heterocyclic systems, including 2,6,7,9-tetrahydro-8H-pyrazolo[5,4,3-de]pyrimido[4,5-e][1,4]diaze