3020-81-3

Usage

Uses

Used in Organic Synthesis:
Butyramidine hydrochloride is used as a reagent for the preparation of new derivatives of pyrimidines, which are important in the development of various chemical compounds and pharmaceuticals. Its role in organic synthesis is crucial for creating novel pyrimidine-based molecules with potential applications in different industries.

InChI:InChI=1/C12H6Cl4S2/c13-7-3-1-4-8(14)11(7)17-18-12-9(15)5-2-6-10(12)16/h1-6H

Upstream product

• 109-74-0 propyl cyanide 
• 2208-08-4 ethyl butyrimidate hydrochloride 

Downstream Products

• 100531-39-3 5-hexyl-2-propyl-1H-pyrimidine-4,6-dione 
• 99167-54-1 2,5-dipropyl-1H-pyrimidine-4,6-dione 
• 98432-22-5 6-amino-2-propyl-3H-pyrimidin-4-one 
• 114426-12-9 5-ethyl-2-propyl-1H-pyrimidine-4,6-dione 
• 105838-94-6 5-pentyl-2-propyl-1H-pyrimidine-4,6-dione 
• 98489-74-8 5-methyl-2-propyl-1H-pyrimidine-4,6-dione 
• 98334-67-9 2-propyl-1H-pyrimidine-4,6-dione 
• 13050-06-1 N,N,N'-Trichlor-butyramidin 
• 1026084-76-3 3-(4-Methyl-6-oxo-2-propyl-1,6-dihydro-pyrimidin-5-yl)-propionic acid ethyl ester 
• 23902-03-6 2-propyl-6,7,8,9-tetrahydro-3H-cyclohepta[d]pyrimidin-4(5H)-one 
• 91272-25-2 2-propyl-5,6,7,8,9,10-hexahydrocycloocta[d]pyrimidin-4(3H)-one 
• 91272-37-6 2-(1-propyl)-5,6-decamethylenepyrimidin-4(3H)-one 
• 72419-29-5 4-Hydroxy-2-propyl-pyrimidine-5-carboxylic acid ethyl ester 
• 148475-54-1 4'-(6-Oxo-2,4-dipropyl-1,6-dihydro-pyrimidin-5-ylmethyl)-biphenyl-2-carbonitrile 

Relevant academic research and scientific papers

Discovery of the bifunctional modulator of angiotensin II type 1 receptor (AT1R) and PPARγ derived from the AT1R antagonist, Fimasartan

Inspired by the well-known PPARγ partial agonism of angiotensin II type 1 receptor (AT1R) antagonists exemplified by an antihypertensive drug, Telmisartan, efforts to identify compounds with the dual activities have been pursued in order to control the two major metabolic disorders, hypertension and hyperglycemia simultaneously. Lead compound 18 derived from the AT1R antagonist, Fimasartan, has successfully presented the possibility to control the medical conditions by a single molecule.

'Green' synthesis of 2-substituted 6-hydroxy-[3H]-pyrimidin-4-ones and 4,6-dichloropyrimidines: Improved strategies and mechanistic study

An improved route to 2-substituted 6-hydroxy-[3H]-pyrimidin-4-ones 4 and to 2-substituted 4,6-dichloropyrimidines 5 is reported. Without using highly toxic reactants, compounds 4 can be prepared conveniently in a one pot synthesis on a one mol scale with average yields up to 80%. 4,6-Dichloropyrimidines 5, which are usually prepared in small quantities, are synthesized with average yields of 80%, using up to 80g of starting material. The mechanism of the chlorination of 4 is investigated computationally for the first time. The results suggest that the chlorination with phosphoryl chloride occurs in an alternating phosphorylation-chlorination manner (pathway 1) which is preferred over a sequence which starts with two phosphorylations. The investigated 4,6-dichloropyrimidines described herein form strong complexes with dichlorophosphoric acid but weak complexes with hydrochloric acid (generated during workup). These latter complexes explain the necessity of using aqueous sodium carbonate during the working up. In order to prevent possible formation of pyrimidinium salts between intermediates or the final dichloropyrimidines and unreacted hydroxypyrimidone, the latter could be deactivated with a strong acid such as dichlorophosphoric acid, thus allowing chlorination but prohibiting salt formation. Because of its general applicability to all nitrogen heterocycle chlorinations with phosphoryl chloride, the proposed route to dichloropyrimidines without solvent or side products, using less toxic reactants, is of general synthetic interest.

Synthesis and antihypertensive activity of pyrimidin-4(3H)-one derivatives as losartan analogue for new angiotensin II receptor type 1 (AT1) antagonists

The discovery, in vitro and in vivo studies of the highly potent AT1 antagonist 12a (BR-A-657, Fimasartan) are presented. A series of pyrimidin-4(3H)-one derivatives as losartan analogue were synthesized and evaluated for a novel class of AT1 receptor antagonists. Among them, 12a containing thioamido moiety displayed both high in vitro functional antagonism and binding affinity [IC50 = 0.42 and 0.13 nM, respectively] and inhibited strongly in vivo AngII-induced pressor response in pithed rats with an ED50 of 0.018 mg/kg. Moreover, in vivo evaluation in furosemide-treated rat and conscious renal hypertensive rat models and the pharmacokinetic study showed that 12a is a highly potent and orally active AT1 selective antagonist having stronger in vivo potency than losartan.

Convenient synthesis and physicochemical profile of new derivatives of pyrimidine

A synthesis of linear oligoheterocycles based on the substituted pyrimidines are described. The desired compounds have been accomplished by the variation of the original Pinner synthesis in which the aliphatic nitrile reacted with hydrogen chloride to give imino ester. These compound reacted with ammonia gas to give amidine. Chalcones in reaction with amidines give bis(phenyl)pyrimidines. The bis(phenyl)pyrimidines reacted with 3,4-ethylenedioxy-2-trimethyltinthiophene or 2-trimethyltinthiophene in the presence of Pd(PPh3)2Cl2 or Pd(PPh3)4 as catalyst to give designed compounds. In this work are presented also some electrochemical measurements using Langmuir-Blodgett technique in mono-and binary systems.

Oxindolylquinazoline derivatives as angiogenesis inhibitors

The invention relates to compounds of formula (I) and salts thereof as further defined herein, wherein ring Z is a 6-membered heterocyclic ring containing 1 to 3 nitrogen atoms, and the use of such compounds and salts to inhibit the effects of VEGF and FGF, and in the treatment of a number of disease states including cancer and rheumatoid arthritis.

PYRIMIDINE DERIVATIVES

Novel pyrimidine derivatives of the formula STR1 represents: either a group: STR2 or a group: STR3 having angiotensin II inhibiting activity.