53681-49-5

Basic information

• Product Name: 6-AMINO-1-BUTYL-1H-PYRIMIDINE-2,4-DIONE
• Synonyms: 6-amino-1-butyl-2,4(1H,3H)-Pyrimidinedione;6-amino-1-butyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
• CAS NO: 53681-49-5
• Molecular Formula: C₈H₁₃N₃O₂
• Molecular Weight: 183.100777
• Mol File: 53681-49-5.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• Density: 1.174 g/cm³
• Refractive Index: 1.519
• CAS DataBase Reference: 6-AMINO-1-BUTYL-1H-PYRIMIDINE-2,4-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-AMINO-1-BUTYL-1H-PYRIMIDINE-2,4-DIONE(53681-49-5)
• EPA Substance Registry System: 6-AMINO-1-BUTYL-1H-PYRIMIDINE-2,4-DIONE(53681-49-5)

Safety Data

• Hazardous Substances Data: 53681-49-5(Hazardous Substances Data)

Usage

Description

6-AMINO-1-BUTYL-1H-PYRIMIDINE-2,4-DIONE, also known as 6-Amino-1-butyluracil, is an organic compound with a unique chemical structure characterized by a pyrimidine ring and an amino group attached to a butyl chain. It is a versatile molecule with potential applications in various fields due to its ability to interact with specific receptors and modulate biological processes.

Uses

Used in Pharmaceutical Industry:
6-AMINO-1-BUTYL-1H-PYRIMIDINE-2,4-DIONE is used as a key intermediate compound for the synthesis of molecules with A2B adenosine receptor antagonistic activity. These molecules have potential therapeutic applications in treating various diseases and conditions, such as asthma, chronic obstructive pulmonary disease (COPD), and other inflammatory disorders, by modulating the adenosine signaling pathway.

InChI:InChI=1/C8H13N3O2/c1-2-3-4-11-6(9)5-7(12)10-8(11)13/h5H,2-4,9H2,1H3,(H,10,12,13)

Upstream product

• 36981-01-8 N-butyl-N'-cyanoacetylurea 
• 592-31-4 1-butyl-urea 
• 105-56-6 ethyl 2-cyanoacetate 
• 372-09-8 cyanoacetic acid 

Downstream Products

• 53681-50-8 6-amino-1-butyl-3-methyluracil 
• 133657-16-6 1-Butyl-7-methyl-5-(3-nitro-phenyl)-2,4-dioxo-1,2,3,4,5,8-hexahydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid methyl ester 
• 628279-11-8 6-amino-1-butyl-3-(2-fluoro-benzyl)-1H-pyrimidine-2,4-dione 
• 628279-12-9 6-amino-1-butyl-3-(3-fluoro-benzyl)-1H-pyrimidine-2,4-dione 
• 161419-78-9 6-amino-3-benzyl-1-butyluracil 
• 81250-15-9 1-Allyl-3-butyl xanthine 
• 81250-24-0 1-propyl-3-butyl-8-methyl xanthine 
• 81250-14-8 1-allyl-3-butyl-8-methyl xanthine 
• 628279-23-2 3-benzyl-5,6-diamino-1H-pyrimidine-2,4-dione 
• 628279-24-3 5,6-diamino-1-butyl-3-(2-fluoro-benzyl)-1H-pyrimidine-2,4-dione 
• 628279-25-4 5,6-diamino-1-butyl-3-(3-fluoro-benzyl)-1H-pyrimidine-2,4-dione 
• 628279-16-3 N-(3-allyl-6-amino-1-butyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-2-phenyl-acetamide 
• 628279-15-2 4-acetylamino-N-(3-allyl-6-amino-1-butyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-benzamide 
• 628279-02-7 N-[4-(1-allyl-3-butyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl)-phenyl]-acetamide 

Relevant articles and documents

XANTHINE DERIVATIVE INHIBITORS OF BET PROTEINS

This invention relates to xanthine derivative compounds that are inhibitors of BET bromodomains proteins, the method of preparation thereof and applications thereof.

Carboxylic acid-catalyzed one-pot synthesis of cyanoacetylureas and their cyclization to 6-aminouracils in guanidine ionic liquid

A novel, one-pot, carboxylic acid-catalyzed synthesis of cyanoacetylureas via in situ generated ureas and their cyclization to 6-aminouracils in the presence of the guanidine-based ionic liquid 1,1,3,3-tetramethylguanidine lactate [TMG][Lac] is described. The ureas were synthesized from amines and potassium cyanate, which on reaction with cyanoacetic acid in the presence of acetic anhydride in the same pot afforded cyanoacetylureas, which undergo cyclization in [TMG][Lac] as solvent as well as catalyst to afford 6-aminouracils. One-pot synthesis of cyanoacetylureas, efficient and rapid cyclization, better yield, shorter reaction time, easy workup procedure, and recyclability of the ionic liquid are some advantages of this procedure.

Selective, high affinity A2B adenosine receptor antagonists: N-1 monosubstituted 8-(pyrazol-4-yl)xanthines

A series of N-1 monosubstituted 8-pyrazolyl xanthines have been synthesized and evaluated for their affinity for the adenosine receptors (AdoRs). We have discovered two compounds 18 (CVT-7124) and 28 (CVT-6694) that display good affinity for the A2B AdoR (Ki = 6 nM and 7 nM, respectively) and greater selectivity for the human A1, A2A, and A3 AdoRs (>1000-, >830-, and >1500-fold; >850-, >700-, and >1280-fold, respectively). CVT-6694 has been shown to block the release of interleukin-6 and monocyte chemotactic protein-1 from bronchial smooth muscle cells (BSMC), a process believed to be promoted by activation of A2B AdoR.