N-METHYLBARBITURIC ACID Chemical Properties

Melting point:

132 °C

Density 

1.379±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Sparingly), Methanol (Slightly)

form 

Solid

pka

pK1:4.35(＋1) (25°C)

color 

White to Off-White

InChI

InChI=1S/C5H6N2O3/c1-7-4(9)2-3(8)6-5(7)10/h2H2,1H3,(H,6,8,10)

InChIKey

DCGGMHIZEAHUJL-UHFFFAOYSA-N

SMILES

C1(=O)N(C)C(=O)CC(=O)N1

Safety Information

HS Code 

2933599590

N-METHYLBARBITURIC ACID Usage And Synthesis

Uses

1-Methylbarbituric Acid is an impurity of Trelagliptin. Trelagliptin (Zafatek) is a pharmaceutical drug used for the treatment of type 2 diabetes.

Synthesis

Acetic anhydride (130 mL, 1.37 mol) was slowly added dropwise to 180 mL of acetic acid solution containing malonic acid (80 g, 0.79 mol) and N-methylurea (50 g, 0.68 mol) at 70 °C. After the dropwise addition was completed, the reaction mixture was warmed up to 90 °C with continuous stirring for 3 hours. After completion of the reaction, the mixture was cooled to room temperature. The solvent was removed by distillation under reduced pressure and the resulting residue was treated with 350 mL of ethanol to precipitate a pale yellow solid. The solid was purified by recrystallization from ethanol to give 63.1 g of 1-methylpyrimidine-2,4,6(1H,3H,5H)-trione as a final crystalline solid (yield: 65.8%). The melting point was measured to be 131.2-133.1 °C (literature value: 130-131.5 °C).

References

[1] Journal of Heterocyclic Chemistry, 2014, vol. 51, # 3, p. 594 - 597
[2] Journal of Medicinal Chemistry, 1989, vol. 32, # 6, p. 1231 - 1237
[3] Patent: WO2009/73210, 2009, A1. Location in patent: Page/Page column 76
[4] Patent: WO2006/133261, 2006, A2. Location in patent: Page/Page column 30
[5] Patent: WO2007/143705, 2007, A2. Location in patent: Page/Page column 23

N-METHYLBARBITURIC ACID(2565-47-1)Related Product Information

• Trelagliptin Impurity 9
• Trelagliptin Impurity 20
• Trelagliptin Impurity 18
• Trelagliptin Impurity 4
• Trelagliptin Impurity 12
• Trelagliptin Impurity 15
• Trelagliptin Impurity 7
• Trelagliptin Impurity 11
• Trelagliptin Related compound 13
• Trelagliptin Impurity 5
• Trelagliptin Impurity 3
• Trelagliptin Impurity 6
• Trelagliptin Impurity 16
• Trelagliptin Impurity 2
• Trelagliptin Impurity 13
• Trelagliptin Impurity 8
• Trelagliptin Impurity 19
• Trelagliptin Impurity 10