6-Hydroxypyrimidine-4-carboxylic acid
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6-Hydroxypyrimidine-4-carboxylic acid
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CAS No:
6299-87-2
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Formula:
C5H4N2O3
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Chemical Name:
6-Hydroxypyrimidine-4-carboxylic acid
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Synonyms:
4-Pyrimidinecarboxylic acid,1,6-dihydro-6-oxo-;4-Pyrimidinecarboxylic acid,6-hydroxy-;1,6-Dihydro-6-oxo-4-pyrimidinecarboxylic acid;6-Hydroxypyrimidine-4-carboxylic acid;NSC 45047;6-Oxo-1,6-dihydropyrimidine-4-carboxylic acid
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CAS No:
6-Hydroxypyrimidine-4-carboxylic acid Basic Attributes
140.09686
140.10
45047
DTXSID40286361
2933599090
Safety Information
24/25
Xi
P264, P280, P305+P351+P338, P33, P313
H319
|Warning|H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]|P264, P280, P305+P351+P338, and P337+P313|Aggregated GHS information provided by 40 companies from 3 notifications to the ECHA C&L Inventory.
6-Hydroxypyrimidine-4-carboxylic acid Use and Manufacturing
In a 1 L round bottom flask, 55 g of sodium ethyloxalacetate (1.05 eq, 0.26 mol) and 26 g of formamidine acetate (1 eq, 0.25 mol) were added to a solution of sodium hydroxide (10 g) in 500 mL of water. The reaction mixture was stirred at room temperature for 16 hours.[00262] Concentrated HCl was added carefully to the mixture until pH = 1, a fine solid precipitated and the reaction mixture was stirred at 0°C for 1 hour. The solid was filtered then washed with water and ether. The white solid was then left in a vacuum oven heated at4OTo a solution of formamidine acetate (10 g, 96 mmol) in 200 mL of water was added diethyl oxalacetate sodium salt (21 g, 100 mmol) and sodium hydroxide (3.8 g, 96 mmol). The reaction mixture was stirred overnight at room temperature, before 6 N HCl was added carefully to adjust PH = 1. The mixture was allowed to stand overnight at 0 °C, and the resultant precipitate was filtered and dried in vacuum to give the desired product (2 g, 15percent) as a red solid. Preparation of -hydroxypyrimidine-^carboxylic acid:; To a suspension of 2.52 g (12.0 mmol) of diethyloxaloacetate sodium salt in 8 mL of water was added 1.9 mL of 6.25 M NaOH(c) 6-hydroxypyrimidine-4-carboxylic acid _:To a solution of sodium (Z)-l, 4-diethoxy-l, 4-dioxobut-2-en-2-olate (55.0 g, 262 mmol) in water (500 mL) was added formamidine acetate (27.3 g, 262 mmol) and sodium hydroxide (10.5 g). After addition, the resulting mixture was stirred at 25 °C for 16 hours then concentrated and then acidified by added aqueous hydrochloric acid (IN) until pH = 1. The resulting solid was collected by filtration, washed with water and ether to give 6- hydroxypyrimidine-4-carboxylic acid (6.0 g, yield: 16.3percent). 1H NMR (400 MHz, DMSO- de) δ 12.89 (s, 1H), 8.24 (s, 1H), 6.83 (s, 1H).
Computed Properties
Molecular Weight:140.10
XLogP3:-1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:140.02219199
Monoisotopic Mass:140.02219199
Topological Polar Surface Area:78.8
Heavy Atom Count:10
Complexity:241
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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6-Hydroxypyrimidine-4-carboxylic acid
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