53681-47-3

Basic information

• Product Name: 6-amino-1-propyluracil
• Synonyms: 6-amino-1-propyluracil;1-Propyl-6-aminouracil;6-Amino-1-propyl-2,4(1H,3H)-pyrimidinedione;6-AMino-1-propyl-3H-pyriMidine-2,4-dione;6-Amino-1-propylpyrimidine-2,4(1H,3H)-dione;6-amino-1-propyl-pyrimidine-2,4-dione;6-amino-1-propylpyrimidine-2,4-dione;6-amino-1-propyl-pyrimidine-2,4-quinone
• CAS NO: 53681-47-3
• Molecular Formula: C₇H₁₁N₃O₂
• Molecular Weight: 169.18114
• EINECS: 258-697-4
• Mol File: 53681-47-3.mol
• Article Data: 16

Chemical Properties

• Melting Point: 279-281℃
• Appearance: /
• Density: 1.212±0.06 g/cm3 (20 ºC 760 Torr)
• Refractive Index: 1.524
• PKA: 9.26±0.40(Predicted)
• CAS DataBase Reference: 6-amino-1-propyluracil(CAS DataBase Reference)
• NIST Chemistry Reference: 6-amino-1-propyluracil(53681-47-3)
• EPA Substance Registry System: 6-amino-1-propyluracil(53681-47-3)

Safety Data

• Hazardous Substances Data: 53681-47-3(Hazardous Substances Data)

Usage

Uses

6-Amino-1-propyluracil is a reactant used in the preparation of pentoxifylline metabolite analogs as antiinflammatory agents.

InChI:InChI=1/C7H11N3O2/c1-2-3-10-5(8)4-6(11)9-7(10)12/h4H,2-3,8H2,1H3,(H,9,11,12)

Upstream product

• 627-06-5 n-propylurea 
• 105-56-6 ethyl 2-cyanoacetate 
• 372-09-8 cyanoacetic acid 
• 41078-07-3 N-cyanoacetyl-N'-propyl-urea 

Downstream Products

• 63981-32-8 6-amino-3-ethyl-1-propylpyrimidine-2,4(1H,3H)-dione 
• 183373-22-0 6-phenyl-1-propyl-7H-pyrrolo[2,3-d]pyrimidin-2,4(1H,3H)-dione 
• 1073239-46-9 6-amino-3-(4-chlorobenzyl)-1-propylpyrimidine-2,4(1H,3H)-dione 
• 1073238-78-4 8-azetidin-1-yl-1-(4-chlorobenzyl)-7-methyl-3-propyl-3,7-dihydro-1H-purine-2,6-dione 
• 1073238-92-2 1-(4-chlorobenzyl)-8-(1-hydroxyethyl)-7-methyl-3-propyl-3,7-dihydro-1H-purine-2,6-dione 
• 1073239-43-6 1-(4-chlorobenzyl)-8-(1-hydroxyethyl)-3-propyl-3,7-dihydro-1H-purine-2,6-dione 
• 1073238-77-3 1-(4-chlorobenzyl)-8-(dimethylamino)-7-methyl-3-propyl-3,7-dihydro-1H-purine-2,6-dione 
• 1073238-90-0 8-bromo-1-(4-chlorobenzyl)-7-methyl-3-propyl-3,7-dihydro-1H-purine-2,6-dione 
• 1073239-50-5 C₁₅H₁₄BrClN₄O₂ 
• 1073238-93-3 1-(4-chlorobenzyl)-7,8-dimethyl-3-propyl-3,7-dihydro-1H-purine-2,6-dione 
• 1073239-45-8 6-amino-3-(4-chlorobenzyl)-5-nitroso-1-propylpyrimidine-2,4(1H,3H)-dione 
• 1073239-44-7 5,6-diamino-3-(4-chlorobenzyl)-1-propylpyrimidine-2,4(1H,3H)-dione 
• 896420-11-4 1-(4-chlorobenzyl)-3-propyl-3,7-dihydro-1H-purine-2,6-dione 
• 131599-05-8 7-Methyl-8-phenyl-3-propyl-3,7-dihydro-purine-2,6-dione 

Relevant articles and documents

Construction of Dihydropyrido[2,3- d]pyrimidine Scaffolds via Aza-Claisen Rearrangement Catalyzed by N-Heterocyclic Carbenes

N-Heterocyclic carbenes (NHCs) catalyzing aza-Claisen rearrangement of α,β-unsaturated enals with cyclic vinylogous amides under oxidative conditions generating potentially biologically active dihydropyridinone-fused uracils have been developed. This strategy represents a unique NHC-activation-based path with the use of 6-aminouracils as stable α,β-diEWG cyclic vinylogous amides for the efficient synthesis of bicyclic N-unprotected lactams similar to those in many useful drugs.

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.

Approach to the library of fused pyridine-4-carboxylic acids by combes-type reaction of acyl pyruvates and electron-rich amino heterocycles

A library of fused pyridine-4-carboxylic acids (including pyrazolo[3,4-b]pyridines, isoxazolo[5,4-b]pyridines, furo[2,3-b]pyridines, thieno[2,3-b]pyridines, and pyrido[2,3-d]pyrimidines) was generated by Combes-type reaction of acyl pyruvates and electron-rich amino heterocycles followed by hydrolysis of the ester. The library members were also demonstrated to undergo the standard combinatorial transformations including amide coupling and esterification, as well as less common heterocyclizations to 1,2,4-triazoles and 1,2,4-oxadiazoles.