1,3-DIMETHYLURACIL-5-CARBOXALDEHYDE Chemical Properties

Melting point:

122-124 °C(Solv: ligroine (8032-32-4))

Boiling point:

274.1±50.0 °C(Predicted)

Density 

1.408±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

solid

pka

-3.06±0.40(Predicted)

Appearance

Light yellow to brown Solid

Sensitive 

Air Sensitive

InChI

InChI=1S/C7H8N2O3/c1-8-3-5(4-10)6(11)9(2)7(8)12/h3-4H,1-2H3

InChIKey

KGJFRZOATIXYPW-UHFFFAOYSA-N

SMILES

C1(=O)N(C)C=C(C=O)C(=O)N1C

1,3-DIMETHYLURACIL-5-CARBOXALDEHYDE Usage And Synthesis

Synthesis

A slurry was formed by suspending 400 mg of 5-formyluracil (2.8 mM) in 10 mL of DMF at room temperature. Subsequently, 280 mg of sodium hydride (7 mM, 60% oil solution) was added to this slurry. After stirring the reaction mixture for 30 minutes, 1.013 g of iodomethane (7.2 mM) was added. After the reaction mixture was transformed from turbid to a homogeneous yellow solution and complete consumption of 5-formyluracil was confirmed by thin layer chromatography (TLC), the reaction was quenched with methanol and water. The reaction mixture was concentrated on a rotary evaporator and the residue partitioned between methanol and hexane. The methanol phase was concentrated and the residue was again partitioned between chloroform and water. The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated to give 420 mg (89% yield) of 1,3-dimethyl-5-formyluracil as an off-white waxy solid. The structure of the product was confirmed by 1H-NMR (DMSO-d6, δ= 9.82 (s, 1H), 8.52 (s, 1H), 3.43 (s, 3H), 3.2 (s, 3H) and LC/MS (retention time = 0.34 min, m/z = 169, [M+H]+).

References

[1] Patent: US2006/19965, 2006, A1. Location in patent: Page/Page column 22
[2] European Journal of Organic Chemistry, 2015, vol. 2015, # 30, p. 6624 - 6630

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