This document summarizes the Pinner pyrimidine synthesis reaction. The reaction involves the condensation of a non-N-substituted amidine and β-keto ester (β-diketone) in the presence of an acid catalyst to form a pyrimidine heterocyclic ring. The mechanism proceeds through protonation, nucleophilic attack, dehydration, and deprotonation steps. Pyrimidine derivatives synthesized via this reaction are used in drugs to treat conditions like malaria, viruses, and cancer.

1. PINNER PYRIMIDINE SYNTHESIS
Presented by:
Jacob Thon Bior
ND0120003
M. Pharm 1st year.
Dept. Pharmaceutical Chemistry.
KLE College of Pharmacy, Belgavi.
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2. CONTENT:
•Introduction
•General Reaction
•Mechanism
•Stepwise explanation
•Applications.
•Reference
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3. INTRODUCTION
Pyrimidine is an aromatic heterocyclic organic compound, six-membered
heterocyclic ring with two nitrogen atoms at position 1 and 3.colourless solid,
weakly basic with melting point of 225.the moiety is uses as antimalaria, antiviral,
anticancer etc….
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N
N 1
2
3
4
5
6
IUPACName:
1,3-diazabenzene

4. General Reaction:
Pinner Pyrimidine reaction is a strong acid- promoted condensation between non-N-
substituted amidine and β-keto ester ( β-diketone) to form a type of nitrogenous
heterocyclic moiety called pyrimidine.
this reaction involves cyclization reaction of amidines with β- diketone molecule in
present of acid as catalyst forming pyrimidine.the most common pyrimidine synthesis
involves the combination of a 1,3-dicarbonyl component with either urea or
amidines/guanidine.
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5. Formation of Amidinium ion
Protonation of amidines molecule led to formation of of amidinium ion
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6. MECHANISM
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7. Stepwise explanation:
1.Protonation.
2.Attack by amidine
3.proton transfer
4.dehydration
5.proton transfer
6.protonation
7.nucleophile attack/cyclization
8.dehydration
9.deprotonation
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8. Drugs with Pyrimidine moiety
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9. APPLICATION
1. Pyrimidine derivatives have been prepared via this reaction procedure amidines react with 1,3-
dicarbonyl compound to form 2,4,6- trisubstituted pyrimidine.
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10. 2. Amidine react with β- keto ester to provide hydroxypyrimidine.
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11. Reference:
Organic Chemistry of Natural Products Vol 1 Gurdeep R.Chatwal Edited by M.
Arora.
Page number 276.
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