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
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$13.00/1g

64-17-5 Synthesis

64-17-5
717 suppliers
$10.00/50g

116436-03-4
86 suppliers
$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