3,N4-ETHENOCYTOSINE Chemical Properties

Density 

1.51±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

7.09±0.20(Predicted)

Appearance

Light brown to brown Solid

3,N4-ETHENOCYTOSINE Usage And Synthesis

Definition

ChEBI: 3,N(4)-ethenocytosine is an organic heterobicyclic compound. It has a role as a mutagen. It is functionally related to a cytosine. It derives from a hydride of an imidazo[1,2-c]pyrimidine.

Synthesis

Procedure for the synthesis of imidazo[1,2-c]pyrimidin-5(6H)-one (13): 50% aqueous chloroacetaldehyde (0.686 mL, 5.40 mmol) was added to a stirred solution of 6-aminopyrimidin-2(1H)-one (500 mg, 4.50 mmol) in N,N-dimethylformamide (DMF, 10 mL). The reaction mixture was stirred at 70 °C for 16 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was washed with ethanol and ether to afford the target compound 13 as a light brown powder (320 mg, 53% yield). Thin layer chromatography (TLC) analysis showed Rf = 0.47 (unfolding agent: ethyl acetate/methanol, 4:1). The melting point of the product was 281-282 °C. Nuclear magnetic resonance hydrogen spectrum (1H NMR, 400 MHz, [D6]DMSO): δ = 6.62 (d, 1H, 3J = 7.6 Hz), 7.28 (d, 1H, 3J = 7.6 Hz), 7.41 (d, 1H, 3J = 1.2 Hz), 7.80 (d, 1H, 3J = 1.2 Hz), 11.6 (bs, 1H). Nuclear magnetic resonance carbon spectrum (13C NMR, 100 MHz, [D6]DMSO): δ = 97.7, 112.2, 129.4, 132.3, 145.9, 146.4. infrared spectrum (IR, KBr): ν = 3451, 3121, 3096, 1718, 1630, 1547, 1290, 1252, 1111 cm- 1. mass spectrum (ESI-MS): m/z 135.8 [M + H]+.

References

[1] Tetrahedron, 2014, vol. 71, # 1, p. 27 - 36
[2] Patent: WO2017/20944, 2017, A1. Location in patent: Page/Page column 16-17

3,N4-ETHENOCYTOSINE(55662-66-3)Related Product Information

• 6-AMINO-IMIDAZO[1,2-A]PYRIMIDINE
• Imidazo[1,2-a]pyrimidine
• Imidazo[1,5-a]pyridine
• Methyl iMidazo[1,2-b]pyridazine-6-carboxylate
• ETHENO-2'-DEOXYCYTIDINE
• 3,N4-ETHENOCYTOSINE
• 2-VINYLIMIDAZOLE
• 1H-Imidazole-1-carboxaldehyde
• ETHENOCYTIDINE
• ETHENOCYTIDINE, [3H]-
• methyl imidazo[1,2-a]pyrimidine-5-carboxylate
• imidazo[1,2-c]pyrimidine-7-carboxylic acid
• Imidazo[1,2-a]pyrimidine-7-carboxylic acid methyl ester