33443-58-2

Usage

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 29, p. 862, 1981 DOI: 10.1248/cpb.29.862

InChI:InChI=1/C12H12N2O2/c1-9-7-11(15)13-12(16)14(9)8-10-5-3-2-4-6-10/h2-7H,8H2,1H3,(H,13,15,16)

Upstream product

• 78224-67-6 2-benzylamino-6-methyl-4H-1,3-oxazin-4-one 
• 155672-68-7 1-benzyl-4-methoxy-6-methyl-2(1H)-pyrimidinone 
• 626-48-2 6-Methyluracil 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 622-77-5 N-benzylcyanamide 
• 100-46-9 benzylamine 
• 2911-21-9 2,4-dioxo-6-methyl-3,4-dihydro-2H-1,3-oxazine 
• 98-88-4 benzoyl chloride 
• 7781-23-9 2,4-dimethoxy-6-methylpyrimidine 
• 91114-97-5 5-acetyl-4-hydroxy-3,6-dihydro-2H-1,3-thiazine-2,6-dione 

Downstream Products

• 585-05-7 oxaluric acid 
• 100-52-7 benzaldehyde 
• 65-85-0 benzoic acid 
• 186387-34-8 1-benzyl-3-(3-chloro-propyl)-6-methyl-1H-pyrimidine-2,4-dione 

Relevant academic research and scientific papers

A Convenient Approach to meso -Uracil-4,4-Difluoro-4-bora-3a, 4a-diaza- s -indacene Derivatives

An effective and convenient protocol for the synthesis of 1-substituted uracil-6-carbaldehyde derivatives has been developed. A three-step sequence permits the preparation of uracil-6-carbaldehydes with various substituents at the N-1 in large quantities by using low-cost precursors. The aldehyde-functionalized uracils served as useful precursors for the preparation of meso-(1-substituted 6-uracil)-derivatives of 4,4-difluoro-4-bora-3a,4a-diaza- s -indacene (BODIPY). In this way, regioselectively functionalized BODIPYs with a direct connection to a nucleobase were prepared in yields of 30-45%. MALDI-TOF mass spectrometry, NMR, UV/vis absorption, and steady-state and time-resolved fluorescence spectroscopies were used to characterize the structures and the spectroscopic/photophysical properties of the resultant dyes.

Selective N1-alkylation of 1,3-dibenzoyluracils: One-pot way to N1-monosubstituted uracil derivatives

A new method for synthesis of N1-monosubstituted uracils and 5- and 6-methyluracil derivatives was developed. It consists in the selective N1-deprotection of N1,N3-dibenzoyluracils in anhydrous dimethylformamide in the presence of potassium carbonate at room temperature and subsequent N1-alkylation by allyl, benzyl or phenacyl type halides or by primary alcohols toluenesulfonates conducted one-pot without isolation of the intermediates. Final N3-debenzoylation by aqueous-alcoholic solution of ammonia affords the corresponding N1-monosubstituted uracil derivatives with overall yields of 52-84%.

FLUORINATED LYSYL OXIDASE-LIKE 2 INHIBITORS AND USES THEREOF

Described herein are compounds that are LOXL2 inhibitors, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds in the treatment of conditions, diseases, or disorders associated with LOXL2 activity.

Azines and azoles: CXXII. New regioselective synthesis of 1-substituted 6-alkyluracils

Readily available 5-acyl-4-hydroxy-3,6-dihydro-2H-1,3-thiazine-2,6-diones with primary alkyl- and arylamines in mild conditions (boiling in propan-2-ol) to give Schiff bases. In more rigid conditions (boiling in DMF), the reaction is accompanied by COS liberation and provides 1-substituted 6-alkyluracils. This previously unknown reaction possesses a considerable synthetic potential and can be considered as a new, general, and regioselective synthetic approach to 1-substituted 6-alkyluracils.

A new synthesis of 1,3-thiazines and their transformation into 1-substituted-6-alkyluracils by extrusion of carbonyl sulfide

A simple synthesis of 5-acyl-4-hydroxy-3,6-dihydro-2H-1,3-thiazine-2,6-diones from malonic acid, potassium thiocyanate and acid anhydrides is described. A new, general, regioselective method for the synthesis of 1-substituted-6-alkyluracils by the reaction of these thiazines with primary alkyl and arylamines is reported.

Synthesis, pharmacology and pharmacokinetics of 3-(4-Arylpiperazin-1-ylalkyl)-uracils as uroselective α1A-antagonists

Predominance in the urethra and prostate of the α1A-adrenoceptor subtype, which is believed to be the receptor mediating noradrenaline induced smooth muscle contraction in these tissues, led to the preparation of α1A-selective antagonists to be tested as uroselective compounds for the treatment of benign prostatic hyperplasia. Thus, a number of selective α1A-adrenoceptor antagonists were synthesized and assayed in vitro for potency and selectivity. Dog pharmacokinetic parameters of 12 (RO700004) and its metabolite 40 (RO1104253) were established. The relative selectivity of intravenously administered 12, 40 and standard prazosin to inhibit hypogastric nerve stimulation-induced increases in intraurethral prostatic pressure versus phenylephrine-induced increases in diastolic blood pressure in anesthetized dogs was 76, 71 and 0.6, respectively.

SYNTHESIS AND ANTIVIRAL ACTIVITY OF ACYCLIC NUCLEOSIDE ANALOGUES OF 6-METHYLURACIL AND 4-ALKYLAMINO-6-METHYL-2(1H)-PYRIMIDINONES

Reaction of 2,4-dimethoxy-6-methylpyrimidine (I) with allyl bromide or benzyl bromide afforded 1-substituted 4-methoxy-6-methyl-2(1H)-pyrimidinone intermediates III, X.Oxidation of the compound III afforded racemic cis diol VI.O-Demethylation and nucleophilic displacement of the intermediates III, VI, and X gave 1-substituted 6-methyluracils IV, VII, IX and 1-substituted 4-alkylamino-6-methyl-2(1H)-pyrimidinones V, VIII, XII in good yields.The compounds II - XII were evaluated against Ranikhet desease virus (RDV); compounds Vb, Vii, X, XIIb - XIId showed 100, 43, 44, 75, 72 and 100percent inhibition, respectively.