2-AMINO-5-CARBOETHOXY-4-HYDROXYPYRIMIDINE Chemical Properties

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 Information

Risk Statements 

36/37/38

Safety Statements 

26-36

HS Code 

2933.59.8000

MSDS

• Language:English Provider:ALFA

2-AMINO-5-CARBOETHOXY-4-HYDROXYPYRIMIDINE Usage And Synthesis

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

2-AMINO-5-CARBOETHOXY-4-HYDROXYPYRIMIDINE(15400-53-0)Related Product Information

• Pyrimidine-5-carboxaldehyde
• 2-AMINO-PYRIMIDINE-5-CARBOXYLIC ACID ETHYL ESTER
• 2-Pyrimidinamine, 5-methyl- (9CI)
• 2-Amino-5-pyrimidinecarboxyaldehyde
• 4-Hydroxypyrimidine-5-carboxylic acid methyl ester
• 5-Pyrimidinemethanol
• METHYL PYRIMIDINE-5-CARBOXYLATE
• 2-Aminopyrimidine-5-carboxylic acid
• 5-METHYLPYRIMIDIN-4-OL
• 5-Pyrimidinecarboxylic acid
• 2-AMINO-5-CARBOETHOXY-4-HYDROXYPYRIMIDINE
• Ethyl 4-hydroxypyrimidine-5-carboxylate
• ETHYL 5-PYRIMIDINECARBOXYLATE 98
• 4-Hydroxypyrimidine
• 4(1H)-Pyrimidinone, 2-amino-5-methyl- (7CI,8CI,9CI)
• Ethyl 2-aminopyrimidine-5-carboxylate
• 5-Pyrimidinemethanol, 2-amino- (9CI)
• ETHYL 4-HYDROXY-2-MORPHOLINOPYRIMIDINE-5-CARBOXYLATE