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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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