heterocyclic chemistry(Name reaction)-Pinner pyrimidine synthesis

1. Pinner Pyrimidine Synthesis
Presentedby:
Anam Ilyas
M.Pharm. 1st semester
(Pharm chemistry)
JAMIA HAMDARD

2. Pinner Pyrimidine Synthesis:
 The condensation of 1,3-dicarbonyl compounds with amidines catalysed by
acids or bases to give pyrimidine derivatives is regarded as the Pinner
pyrimidine synthesis.

3. HISTORICALPERSPECTIVE:
 In the 1880s, Pinner found that the amidine derivativereacted with acetoacetic ester to
give 2-substituted-6-hydroxy-4-methylpyrimidine.

4. MECHANISM

6. SYNTHETIC UTILITY OF PINNER
PYRIMIDINE SYNTHESIS
 Many pyrimidine derivatives have been prepared viathe pinner
procedure.
1. Amidines react with Acetylacetone to form 2,4,6-Trisubstitutedpyrimidines.
K2CO3

7. 2. Amidines react with B-ketoester to provide hydroxypyrimidines.

8. SULFAMERAZINE
 Molecular formula: C11H12N4O2S
 Sulfamerazine is also known as solumedine.
 Sulfamerazine belongs to antimicrobial drugs that contain sulfonamide as a parent structure.

9. USES OF SULFAMERAZINE:
It is used as an antibacterial agent.
It can be used to treat :
1. bronchitis
2. Prostatitis
3. urinary tract infections.
SIDE EFFECTS OF SULFAMERAZINE:
1. Nausea
2. Vomiting
3. Diarrhea
4. hypersensitivity reactions.
5. Hematologic effects such as anemia.

10.  MECHANISM OF ACTION:
 Sulfamerazine act by inhibiting bacterial folic
acid synthesis by competing PABA with
Dihydrofolate Synthetase.
 It is a competitive inhibitor of dihydrofolate
synthetase, this enzyme is used in folate
synthesis is bacteria and therefore sulfamerazine
interferes with this pathway and ultimately
decreasing the synthesis of bacterial nucleotides
and DNA.

11. SYNTHESIS OF SULFAMERAZINE
➢ It is a 3 step process:
 Preparation of ASC(p-Acetamidobenzne chloride)
 2-Preparation of 2-Amino-4-methyl pyrimidine
 Condensation of ASC and 2-Amino-4-methyl pyrimidine followed by
alkaline hydrolysis

12.  STEP1: Preparation of ASC(p-Acetamidobenzne chloride)

13.  STEP2: 2-Preparation of 2-Amino-4-methyl pyrimidine
It is achived by the interation of sodium derivative of Formyl acetone with guanidine.

14.  STEP 3:Alkaline Hydrolysis:
condensation of ACE and 2-Amino-4-methyl Pyrimidine takesplace followed by Alkaline Hydrolysis.

15. TRIMETHOPRIM
2,4-diamino-5-(3,4,5-trimethoxybenzyl)pyrimidine
MOLECULAR FORMULA: C14H18N4O3

16. USES OF TRIMETHOPRIM:
Trimethoprim is a bacteriostatic antibiotic.
1. It is active against many aerobic gram negetive bacilli and a few
gram positive organism.
2. trimethoprim is indicated for the treatment of acute episodes of
uncomplicated urinary tract infections.
SIDE EFFECTS OF TRIMETHOPRIM:
1. Folate deficiency result in megaloblastic anaemia.
2. Nausea, Vomitting, Skin rashes.

17. Mechanism Of
Action:
 Trimethoprim is a
bacteriostatic antibiotic.
 It is active against many
aerobic gram negative
bacilli
 It is >50,000 more active
against Bacterial DHFRase
than Mammalian enzyme.
 It selectively inhibits
bacterial dihydrofolate
reductase (DHFRase).

18. SYNTHESIS OF TRIMETHOPRIM:

19. THANK YOU