ChemicalBook CAS DataBase List 2,4-DIAMINO-6-ETHOXYPYRIMIDINE

2,4-DIAMINO-6-ETHOXYPYRIMIDINE synthesis

6synthesis methods

Product Name:2,4-DIAMINO-6-ETHOXYPYRIMIDINE
CAS Number:116436-03-4
Molecular formula:C6H10N4O
Molecular Weight:154.17

156-83-2

64-17-5

116436-03-4

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.

156-83-2
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$13.00/1g

64-17-5 Synthesis

64-17-5
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$10.00/50g

116436-03-4
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$35.00/100mg

Yield: 75%

Reaction Conditions:

with sodium hydride for 6 h;Reflux;

Steps:

5.2.2. 6-Ethoxypyrimidine-2,4-diamine (1b)
To a solution of NaH (2.77 g, 69.2 mmol) in ethanol (150 ml) was added 2,6-diamino-4-chloropyrimidine (5.0 g, 34.6 mmol). The mixture was refluxed for 6 h. After cooling, the solution was neutralized with a 5-6 N HCl solution in isopropyl alcohol. After removing the solvents in vacuo, the residue was purified by chromatography on silica gel (CH₂Cl₂/MeOH 40:1), yielding the title compound as a white solid (4.0 g, 75%). Mp 164-165 °C. ¹H NMR (300 MHz, DMSO, 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, CH₂), 1.22 (t, J = 7.1 Hz, 3H, CH₃) ppm. ¹³C NMR (75 MHz, DMSO, 25 °C): δ = 170.0, 165.9, 162.9, 76.1, 60.2, 14.7 ppm. HRMS: calcd for C₆H₁₁N₄O [M+H]⁺ 155.09329, found 155.09260.

References:

Jang, Mi-Yeon;Jonghe, Steven De;Segers, Kenneth;Anné, Jozef;Herdewijn, Piet [Bioorganic and Medicinal Chemistry,2011,vol. 19,# 1,p. 702 - 714] Location in patent:experimental part

425-75-2 Synthesis