heterocyclic chemistry
TRANSCRIPT
Heterocyclic chemistry
• Prepared by ganesh mote• Asst professor at arvind gavali college of
pharmacy,satara
PYRIMIDINE
• Physical properties of Pyrimidine1. Pyrimidine is a colourless compounds2. Melting point-225°c 3. Boiling point-124°c4. It is weakly basic as compared to pyridine or imidazole 5. The decrease in its basicity is due to the electron
withdrawing effectof secon hydrogenpresent in the ring
N
N
pyrimidine
Resonance theory for pyrimidine
N
N
N
N
N
N
N
N
N
N
N
N
N
N
N
N
CH2
C
C
O
OOC2H5
OC2H5 NH2
C
H2N
O
NaOC2H5
-C2H5OH
NH
NH
O
O O
N
N
1.FROM MALONIC ESTER
N
N
Cl
Cl
CH
HC
COOH
H3CNH2
C
H2N
O
Base
-H2OCOOHNH2
HN OH3C
NH
HN
O
O
H3C
H2,Pd
-H2O
Br2
Crotonic acidurea
C
C6H5
O
H3C
BaseC
C6H5
O
-H2C
C
O
H2NH
-H2O
NH2
O
C6H5
HCONH2
formamide
2,4-dichloropyrimidine pyrimidine
pyrimidine-2,4,6(1H,3H,5H)-trioneurea
diethyl malonate
(Z)-3-amino-1-phenylprop-2-en-1-one
-H2O
Redn
SYNTHESIS OF PYRIMIDINE
A.Electrophilic substitution reaction
N
N Br2
N
N
Br
HNO3
N
N
O2N
SO3
N
N
HO3S
3HC C
O
Cl
N
N
C
O
H3C
5-bromopyrimidine
1-(pyrimidin-5-yl)ethanone
pyrimidine-5-sulfonic acid
5-nitropyrimidine
B.Nucleophilic substitution
N
N
N
N
N
N
N
N
N
N
NaNH2
NH2
NaOH
OH
n-Butyl lithiun
CH2CH2CH2CH3
C6H5MgBr
C6H5
pyrimidin-2-ol
pyrimidin-2-amine
2-butylpyrimidine
2-phenylpyrimidine
C.Reaction with acid and Oxidation
N
N
NH
NH CH3COOOH
N
N
O
HCl
1,2,3,4-tetrahydropyrimidine
pyrimidine
N-OXIDE PYRIMIDINE
Application of pyrimidine
• It is derivatives of barbituric acid used as antipsychotic agent and antiepileptic agent
• Some sulpha drugs contains pyrimidine nucleus e.g sulphadiazine used as antibacterial agents
• Biological importance is pyrimidine act as nitrogen base in synthesis of DNA.E.g cytocine,thymine,uracil
• Folic acid is responsible blood and female.hence pyrimidine nucleus is present in folic acid vitamin
• Riboflavin is Vit B2.hence pyrimidine is present in riboflavin