2-methoxy-5-nitropyrimidine Chemical Properties

Melting point:

168-169 °C

Boiling point:

305.3±34.0 °C(Predicted)

Density 

1.388±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

-1.99±0.22(Predicted)

2-methoxy-5-nitropyrimidine Usage And Synthesis

Synthesis

1. Synthesis of 2-methoxy-5-nitropyrimidine: 2-chloro-5-nitropyrimidine (0.486 g, 3.03 mmol) was added to a methanol (12 mL) solution of sodium methanolate (0.090 g sodium) and heated at reflux for 1 hour. After cooling, the reaction mixture was concentrated under vacuum, extracted with ethyl acetate and washed with water. The aqueous layer was then extracted with chloroform, the organic layers were combined, dried with sodium sulfate and concentrated to give 2-methoxy-5-nitropyrimidine in yellow powder form (0.347 g, 75% yield). 2. Synthesis of 5-amino-2-methoxypyrimidine: the above nitro compound (0.342g, 2.20mmol) was dissolved in methanol (20mL), 10% Pd/C (0.30g) was added, and stirred for 18 hours under a hydrogen atmosphere (25 inches/hour). The reaction mixture was filtered through diatomaceous earth and concentrated to give 5-amino-2-methoxypyrimidine (0.274 g, 100% yield) as colorless oil. 3. Synthesis of target compound: The above amino compound (0.274 g, 2.19 mmol) was dissolved in tetrahydrofuran (3 mL), 1.25 mL NaHMDS (2M THF solution) was added and stirred for 10 min. A THF (5 mL) solution of 1-[4-chloro-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-2-(difluoromethyl)-4-methoxy-1H-benzimidazole (0.31 g, 0.78 mmol) was added and stirring was continued for 90 min. The reaction mixture was neutralized with acetic acid, diluted with water and extracted with ethyl acetate. The organic layer was washed with water and ammonia, dried and concentrated. Recrystallization from ethanol/dichloromethane gave the target compound (0.098 g, 26% yield).

References

[1] Patent: US2011/9405, 2011, A1. Location in patent: Page/Page column 55-56
[2] Journal of the American Chemical Society, 1942, vol. 64, p. 567,569,570
[3] Australian Journal of Chemistry, 1966, vol. 19, p. 2321,2326
[4] Patent: WO2005/3100, 2005, A2. Location in patent: Page 135

2-methoxy-5-nitropyrimidine(14001-69-5)Related Product Information

• Sodium Methoxide
• 2,4,6-TRIMETHOXY-5-NITROPYRIMIDINE
• 2-Methoxypyrimidin-5-amine
• 2-METHOXY-5-NITROPYRIMIDIN-4-AMINE
• 2-methoxy-5-nitropyrimidine
• 5-NITRO-PYRIMIDIN-2-OL
• 2,4-DIMETHOXY-5-NITRO-PYRIMIDINE