| Identification | More | [Name]
2-AMINO-5-CARBOETHOXY-4-HYDROXYPYRIMIDINE | [CAS]
15400-53-0 | [Synonyms]
2-AMINO-5-CARBOETHOXY-4-HYDROXYPYRIMIDINE
ETHYL 2-AMINO-4-HYDROXYPYRIMIDINE-5-CARBOXYLATE
LABOTEST-BB LT00455352
2-Amino-5-ethoxycarbonyl-4-hydroxypyrimidine~2-Amino-4-hydroxypyrimidine-5-carboxylic acid ethyl ester~Ethyl 2-amino-4-hydroxypyrimidine-5-carboxylate
ethyl 2-amino-1,4-dihydro-4-oxopyrimidine-5-carboxylate
2-Amino-4-hydroxypyrimidine-5-carboxylicacidethylester
2-Amino-5-ethoxycarbonyl-4-hydroxypyrimidine
2-Amino-5-carboethoxy-4-hydroxyprimidine
2-Amino-5-carbethoxyl-4-hydroxypyrimidine
2-Amino-1,4-dihydro-4-oxo-5-pyrimidinecarboxylic acid ethyl ester
2-Amino-4-hydroxy-5-pyrimidinecarboxylic acid ethyl ester | [EINECS(EC#)]
239-418-5 | [Molecular Formula]
C7H9N3O3 | [MDL Number]
MFCD00039708 | [Molecular Weight]
183.16 | [MOL File]
15400-53-0.mol |
| Chemical Properties | Back Directory | [Melting point ]
300°C (dec.) | [density ]
1.48±0.1 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2–8 °C | [form ]
powder to crystal | [pka]
8.26±0.50(Predicted) | [color ]
White to Orange to Green | [BRN ]
165835 | [InChIKey]
HRRHGLKNOJHIGY-UHFFFAOYSA-N | [CAS DataBase Reference]
15400-53-0(CAS DataBase Reference) |
| Safety Data | Back Directory | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [HS Code ]
2933.59.8000 |
| Hazard Information | Back Directory | [Definition]
ChEBI: An aminopyrimidine that is 2-amino-4-hydroxypyrimidine in which the hydrogen at position 5 is substituted by an ethoxycarbonyl group. | [Synthesis]
In a 20 L three-necked flask, 1.070 Kg of potassium hydroxide (KOH) was dissolved in 10 L of distilled water and stirred until completely dissolved to form a clarified solution. Subsequently, 5 g of silica-functionalized magnetic nanoparticles (Fe3O4@SiO2) were added to the solution. Under continuous stirring, 2 Kg of guanidine carbonate was added to the above mixture to ensure its complete dissolution. The temperature of the reaction system was maintained at around 20°C. Over a period of 3 hours, 2.4 kg of diethyl ethoxymethyl malonate was slowly added dropwise while the reaction temperature was gradually increased from 20 °C to 35 °C. A yellow solid precipitated during the reaction and the reaction mixture was subsequently cooled. The Fe3O4@SiO2 particles were separated and removed using an external magnet and the particles were washed with acetone and dried. The reaction mixture was further cooled to 0-5°C and filtered to obtain a light yellow consistency, which was washed well with ice water. The crude product was recrystallized by ethanol/water solvent mixture and dried in an oven at 40°C. The dried product was divided into two parts and dissolved in 15 L of 60% water/40% ethanol mixed solvent for secondary recrystallization. The initial recrystallized solution was turbid and was clarified by steam heating for 1 hour. Subsequently, the solution began to crystallize at 39°C and was slowly cooled to room temperature. The above recrystallization process was repeated for both parts of the product and the final product was dried in a vacuum oven. Yield: 95%. | [References]
[1] Asian Journal of Chemistry, 2017, vol. 29, # 10, p. 2119 - 2122
[2] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 14, p. 4841 - 4856
[3] Patent: US6194419, 2001, B1 |
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