6-Azauracil

white to light yellow fine crystalline powder

6-azauracil is a 1,2,4-triazine compound having oxo-substituents at the 3- and 5-positions. It has a role as an antimetabolite. It is a member of 1,2,4-triazines and a nucleobase analogue.

Poison by intraperitoneal route. Experimental reproductive effects. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

Weigh 2-[2-(aminocarbonyl) fluorenylene]33.9 g (0.259 mol) and sodium hydroxide 51 g (1.275 mol)Soluble in 150mlIn ethylene glycol, The mixture was stirred under magnetic stirring at 80 ° C for 12 h.After cooling by cooling water, Add 250ml of methanol, Allow to stand for 12h, After suction filtration, Solvent recovery, 41.9 g of wet product were obtained, Dissolved in 60ml of water, Adjust pH to pH <3 with hydrochloric acid, Then heated to 80 ° C, After stirring for half an hour, Cool down to 10 ° C with ice brine.After suction filtration and rinsing with ultrapure water, Vacuum drying gave 6-aza-uracil (CD-2) 18 g (0.159 mol, yield: 61.6percent).1) 6-Bromo-2H-f 1, 2, 41tri azi ne-3, 5-d i one (2i); 2H- [1, 2, 4] triazin-3, 5-dione (50 g, 442 mmol) is placed in the presence of 60 ml of bromine in 800 ml of water at 60C for 10 h. The reaction medium is then run slowly onto a solution of aqueous ammonia until pH = 5. It is then extracted with ethyl acetate and the organic phases are dried over MgS04. After filtration and concentration to dryness, 2i is isolated in the form of a white solid (79.2 g, yield = 93%). TLC Merck silica gel 60 F 254, CH2CI2-MeOH : 90-10, Rf = 0.32.Intermediate 1:; a) 6-Bromo-2H-[1, 2, 4]triazine-3, 5-dione (1a); 2H-[1, 2, 4]triazin-3, 5-dione (50 g, 442 mmol) is placed in the presence of 60 ml of bromine in 800 ml of water at 60 C. for 10 h. The reaction medium is then slowly added to an ammonia solution until pH=5. It is then extracted in ethyl acetate and the organic phases are dried on MgSO4. After filtration and dry concentration, 1a is isolated in the form of a white solid (79.2 g, yield=93%). TLC silica gel 60 F 254 Merck, CH2Cl2:MeOH 90:10, Rf=0.32.A mixture of 25 g of Example A7; a) Preparation of intermediate 16; A mixture of 25 g (217 mmoles) of A mixture of A mixture of compound I (43.4 mmol), bromine (5 mL) and water (75 mL) is stirred at room temperature for 7 hours. Then the precipitate was filtered to give compound 4(7.5g). 1.3. 6-bromo-Intermediates 1 : a) 6-bromo-2H- [1, 2, 4] triazine-3, 5-dione (Ia)H2H- [1, 2, 4] triazin-3, 5-dione (20 g, 177 mmol) is placed in the presence of pyridinium perbromide in 200 mL of water at 900C for 4 h. The reaction medium is then extracted with ethyl acetate and the organic phases are dried on MgSO4. After filtration and dry concentration, Ia is isolated as a white solid (27 g, yield=80%) . TLC silica gel 60 F 254 Merck, CH2Cl2-MeOH: 90-10, Rf = 0.32.Preparation of Intermediate I-06.A mixture of Preparation of Intermediate I-06 [0247] [0248] A mixture of To a solution of Bromine (2.506 mL, 48.6 mmol) was added to a suspension of 1 , 2, 4-triazine-3, 5(2H, 4H)- dione (commercially available from Aldrich, 2.5 g, 22.11 mmol) in Water (40 mL). The According to Scheme 2 Step 1: To a stirred suspension of 2 g of 6-azauracyl (17.7 mmol) and water (15 mL) was added 2 mL of bromine (38.9 mmol) at room temperature. The mixture was stirred for 48 h at room temperature and filtered. The crude solid was washed with water and dried to afford 2(A) as a white powder (2.3 g, 11% yield).LC1: Rt=0.69-1.53MS m/z (ES) [M-H]-=189.9, 191.95-Bromo-

6-Azauracil (6-AU) is used as a growth inhibitor of various microorganisms via depletion of intracellular GTP and UTP nucleotide pools. 6-Azauracil has been widely used in investigations on modulation of transcription, especially in yeast models.

Molecular Weight:113.08
XLogP3:-0.6
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Exact Mass:113.022526347
Monoisotopic Mass:113.022526347
Topological Polar Surface Area:70.6
Heavy Atom Count:8
Complexity:162
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes