4214-72-6

Usage

Uses

Used in Pharmaceutical Industry:
2-Pyrimidinamine, N-(1-methylethyl)(9CI) is used as a neurotropic agent for the treatment of neurological disorders. It prevents synaptic remodeling by suppressing the formation of redundant nerve endings from additional axons, thus maintaining the stability of neural connections.
Used in Drug Metabolism Studies:
Isaxonine is transformed by cytochrome P450 into reactive metabolites, which can lead to immunoallergic hepatitis in humans. This property makes it a valuable compound for studying drug metabolism, drug-drug interactions, and the development of safer pharmaceuticals.

Originator

Nerfactor,Ipsen,France,1981

Manufacturing Process

6 liters of ethanol and 685 g (5 mold of 2-isopropylamino pyrimidine were added to a 10 liter reactor and stirred. To the solution were added 600 g (5.2 mols) of phosphoric acid and the mixture was boiled under reflux for one hour. There was obtained a dark green solution which was treated with 30 g of carbon black. After separation and crystallization while stirring overnight, the crystallized product was separated, washed with ethanol and dried at 50°C. There was obtained 1,027 g (87% yield) of a white powder melting at 125°C. The analysis of the compound showed a good correspondence with the formula C7H14O4N3P.

Therapeutic Function

Neurotropic

World Health Organization (WHO)

Isaxonine phosphate was introduced in 1981 and marketed exclusively in France for the treatment of peripheral neuropathy. In January 1983 indications for use were restricted following its association with cases of toxic hepatitis. It was subsequently withdrawn in June 1983.

InChI:InChI=1/C7H11N3/c1-6(2)10-7-8-4-3-5-9-7/h3-6H,1-2H3,(H,8,9,10)

Upstream product

• 1722-12-9 2-chloropyrimidine 
• 2016-57-1 1-aminodecane 
• 75-31-0 isopropylamine 

Downstream Products

• 1048338-59-5 isopropyl-(5-phenyl-pyrimidin-2-yl)-amine 
• 1313613-63-6 Br^(1-)*C₁₅H₁₈N₃O⁽¹⁺⁾ 
• 77476-95-0 (5-bromopyrimidin-2-yl)-N-isopropylamine 
• 1042274-96-3 2-(1,1'-biphenyl-4-yl)-2-hydroxy-1-isopropyl-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-4-ium bromide 

Relevant academic research and scientific papers

Palladium-catalyzed remote C-H functionalization of 2-aminopyrimidines

A straightforward strategy was developed for the arylation and olefination at the C5-position of the N-(alkyl)pyrimidin-2-amine core with readily available aryl halides and alkenes, respectively. This approach was highly regioselective, and the transformation was achieved based on two different (Pd(ii)/Pd(iv)) and (Pd(0)/Pd(ii)) catalytic cycles.

COMPOSITIONS PROVIDING ENHANCED ANTIBACTERIAL ACTIVITY AGAINST GRAM-POSITIVE BACTERIA AND USE THEREOF

A method of inhibiting, reducing growth of or destroying gram positive bacteria comprising contacting the gram positive bacteria with an effective amount of a 2-(substituted-amino)-imidazole compound and with an additional antibacterial compound separatel

Structure-activity relationship of 4(5)-aryl-2-amino-1 H -imidazoles, N 1-substituted 2-aminoimidazoles and imidazo[1,2- a ]pyrimidinium salts as inhibitors of biofilm formation by salmonella typhimurium and pseudomonas aeruginosa

A library of 112 4(5)-aryl-2-amino-1H-imidazoles, 4,5-diphenyl-2-amino-1H- imidazoles, and N1-substituted 4(5)-phenyl-2-aminoimidazoles was synthesized and tested for the antagonistic effect against biofilm formation by Salmonella Typhimurium and Pseudomo

A divergent synthesis of substituted 2-aminoimidazoles from 2-aminopyrimidines

(Chemical Equation Presented) A new divergent and efficient synthesis of substituted 2-aminoimidazoles 5 and 6 has been developed starting from the readily available 2-aminopyrimidines 1 and α-bromocarbonyl compounds 2, using conventional heating or microwave irradiation. Thus, the cleavage of 1,2,3-substituted imidazo[1,2-a]pyrimidin-1-ium salts 4 with hydrazine or secondary amines led to 1,4,5-trisubstituted 2-aminoimidazoles 5, when the hydrazinolysis of 2-hydroxy-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-4-ium salts 3, followed by a novel Dimroth-type rearrangement, resulted in formation of 2-amino-1H-imidazoles 6. The relevant pathway of transformations was identified by characterization of the intermediates.

Gas-phase pyrolytic reactions of N-ethyl, N-isopropyl, and N-t-butyl substituted 2-aminopyrazine and 2-aminopyrimidine

The rates of gas-phase elimination of N-ethyl (1), N-isopropyl (2), N-t-butyl (3) substituted 2-aminopyrazine and N-ethyl (4), N-isopropyl (5), and N-t-butyl (6) substituted 2-aminopyrimidine have been measured. The compounds undergo unimolecular first-order pyrolytic reactions. The relative rates of the primary:secondary:tertiary alkyl homologues at 600 K are 1:14.4:38.0 for the pyrazines and 1:20.8:162.5 for the pyrimidines, respectively. The reactivities of these compounds have been compared with those of the alkoxy analogues and with each other. Product analyses, together with the kinetic data, were used to outline a feasible pathway for the elimination reaction of the compounds under study.

Preparation of 2-isopropylamino pyrimidine

The invention provides a process for the preparation of 2-isopropylamino-pyrimidine, the process comprising reacting bis(isopropylguanidine)sulphate with 1,1,3,3-tetraethoxy-propane in stoichiometric proportions at 40°-60° C., in acidic aqueous solution.