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Ethyl 4-hydroxypyrimidine-5-carboxylate

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CAS:4786-52-1
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Ethyl 4-hydroxypyrimidine-5-carboxylate Basic information
Product Name:Ethyl 4-hydroxypyrimidine-5-carboxylate
Synonyms:6-Hydroxypyrimidine-5-carboxylic acid ethyl ester;4-hydroxy-5-pyrimidinecarboxylicaciethylester;ETHYL 4-HYDROXYPYRIMIDINE-5-CARBOXYLATE;6-OXO-1,6-DIHYDRO-PYRIMIDINE-5-CARBOXYLIC ACID ETHYL ESTER;4-HYDROXY-PYRIMIDINE-5-CARBOXYLIC ACID ETHYL ESTER;5-Pyrimidinecarboxylic acid, 1,4-dihydro-4-oxo-, ethyl ester;Ethyl 6-oxo-1,6-dihydropyrimidine-5-carboxylate LR;Ethyl 1,4-dihydro-4-oxo-5-pyrimidinecarboxylate
CAS:4786-52-1
MF:C7H8N2O3
MW:168.15
EINECS:
Product Categories:pharmacetical;Heterocycle-Pyrimidine series;CMLLYL
Mol File:4786-52-1.mol
Ethyl 4-hydroxypyrimidine-5-carboxylate Structure
Ethyl 4-hydroxypyrimidine-5-carboxylate Chemical Properties
Melting point 185-186 °C
density 1.33±0.1 g/cm3(Predicted)
storage temp. Inert atmosphere,Room Temperature
pka7.70±0.40(Predicted)
AppearanceLight yellow to yellow Solid
InChIInChI=1S/C7H8N2O3/c1-2-12-7(11)5-3-8-4-9-6(5)10/h3-4H,2H2,1H3,(H,8,9,10)
InChIKeyPLMIZYMXBHSARX-UHFFFAOYSA-N
SMILESC1NC(=O)C(C(OCC)=O)=CN=1
Safety Information
HazardClass IRRITANT
HS Code 2933599590
MSDS Information
Ethyl 4-hydroxypyrimidine-5-carboxylate Usage And Synthesis
Uses7-Chloroisoquinolin-1(2H)-one acts as a reagent for the preparation, SAR of methoxyisoquinoline derivative and discovery of asunaprevir (BMS-650032), an orally efficacious NS3 protease inhibitor for the treatment of hepatitis C virus infection. Synthesis and pharmacological evaluation of a series of 1,2-dihydro-1-[(5-methyl-1-imidazol-4-yl)methyl]-2-oxopyridine 5-HT3 antagonists.
Synthesis

Ethyl 4-hydroxy-5-pyrimidinecarboxylate was prepared as follows: 

Add 1.6g (70mmol) of sodium metal to 50mL of anhydrous ethanol, wait for the reaction to be complete, ice-water bath cooled to 0??C, add 7.3g (70mmol) formamidine acetate, followed by the slow dropwise addition of 15.1g (70mmol) diethyl ethoxymethylidene malonate , the reaction was continued at 0 ??C for 3 h. 1.6 g (70 mmol) of sodium metal dissolved in 50 mL of anhydrous ethanol was cooled to 0 ??C and added dropwise to the above reaction solution. After the reaction at room temperature overnight, the majority of the ethanol was removed to give a yellow solid. It was added to 100mL of water, heated until dissolved, and when cooled, 100mL of ether was added, stirred thoroughly, and the ether was separated to remove the raw material that had not reacted completely. Continue to heat to dissolve, use concentrated hydrochloric acid to adjust the pH of the solution to 2 ~ 3, after cooling, precipitated light yellow solid, filtered, vacuum dried, and finally obtained 9.4g of light yellow solid, the yield was 80%.

Ethyl 4-hydroxypyrimidine-5-carboxylate Preparation Products And Raw materials
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