Pinner pyrimidine synthesis

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1. PINNER PYRIMIDINE SYNTHESIS Presented by: Jacob Thon Bior ND0120003 M. Pharm 1 st year. Dept. Pharmaceutical Chemistry. KLE College of Pharmacy, Belgavi. 1 Department Of Pharmaceutical Chemistry

2. CONTENT: Introduction General Reaction Mechanism Stepwise explanation Applications. Reference 2 Department Of Pharmaceutical Chemistry

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…. 3 Department Of Pharmaceutical Chemistry

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. 4 Department Of Pharmaceutical Chemistry

5. Formation of Amidinium ion Protonation of amidines molecule led to formation of of amidinium ion 5 Department Of Pharmaceutical Chemistry

6. MECHANISM 6 Department Of Pharmaceutical Chemistry

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 Department Of Pharmaceutical Chemistry 7

8. Drugs with Pyrimidine moiety Department Of Pharmaceutical Chemistry 8

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. 9 Department Of Pharmaceutical Chemistry

10. 2. Amidine react with β - keto ester to provide hydroxypyrimidine. Department Of Pharmaceutical Chemistry 10

11. Reference: Organic Chemistry of Natural Products Vol 1 Gurdeep R.Chatwal Edited by M. Arora . Page number 276. 11 Department Of Pharmaceutical Chemistry