2,4-DIAMINO-6-ETHOXYPYRIMIDINE Chemical Properties

Melting point:

160 °C(Solv: water (7732-18-5))

Boiling point:

420.8±48.0 °C(Predicted)

Density 

1.274±0.06 g/cm3(Predicted)

storage temp. 

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

pka

5.41±0.10(Predicted)

Appearance

Light yellow to yellow Solid

2,4-DIAMINO-6-ETHOXYPYRIMIDINE Usage And Synthesis

Synthesis

To a suspension of sodium hydride (2.77 g, 69.2 mmol) in anhydrous ethanol (150 mL) was added 2,4-diamino-6-chloropyrimidine (5.0 g, 34.6 mmol) in batches. The reaction mixture was heated to reflux and kept for 6 hours. After completion of the reaction, it was cooled to room temperature and the reaction solution was neutralized with an isopropanol solution of 5-6 N hydrochloric acid. The solvent was removed by concentration under reduced pressure and the resulting residue was purified by silica gel column chromatography (eluent: dichloromethane/methanol=40:1, v/v) to afford 2,4-diamino-6-ethoxypyrimidine as a white solid (4.0 g, 75% yield). The melting point of the product was 164-165 °C. 1H NMR (300 MHz, DMSO-d6, 25 °C): δ 6.00 (s, 2H, NH2), 5.88 (s, 2H, NH2), 5.03 (s, 1H, CH), 4.13 (q, J=7.1 Hz, 2H, OCH2CH3), 1.22 (t, J=7.1 Hz, 3H OCH2CH3).13C NMR (75 MHz, DMSO-d6, 25°C): δ 170.0 (C), 165.9 (C), 162.9 (C), 76.1 (CH), 60.2 (OCH2CH3), 14.7 (OCH2CH3). High resolution mass spectrometry (HRMS): calculated value C6H11N4O [M+H]+ 155.09329, measured value 155.09260.

References

[1] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 1, p. 702 - 714
[2] Patent: US2004/77859, 2004, A1. Location in patent: Page 23
[3] Organic and Biomolecular Chemistry, 2010, vol. 8, # 10, p. 2397 - 2407
[4] Journal of the American Chemical Society, 1951, vol. 73, p. 2864,2867
[5] Journal of Organic Chemistry, 2005, vol. 70, # 7, p. 2729 - 2738

2,4-DIAMINO-6-ETHOXYPYRIMIDINE(116436-03-4)Related Product Information

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• 2-Amino-4-isopropoxy-6-(methylamino)-5-nitroso-pyrimidine
• 4-CYCLOHEXYLMETHOXY-2,6-DIAMINO-5-NITROSOPYRIMIDINE
• N-[4-(2,6-Diamino-pyrimidin-4-yloxymethyl)-benzyl]-2,2,2-trifluoro-acetamide
• 2,4-BIS(ACRYLAMIDO)-6-ETHOXYPYRIMIDINE
• 2,4-diamino-6-(benzyloxy)pyrimidine-5-carbonitrile
• 2,4-diamino-6-ethoxy-5-pyrimidinecarbonitrile
• N-[4-AMINO-5-NITROSO-6-(PENTYLOXY)PYRIMIDIN-2-YL]-N-METHYLAMINE
• 2,4-DIAMINO-6-ETHOXYPYRIMIDINE