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With caesium carbonate In N,N-dimethyl-formamide at 60℃; for 7 h; Inert atmosphere
6-amino-9-ethyl-9H-purine was synthesized by the addition of ethyl iodide (3.6 ml, 45 mmol) to a white suspension of adenine (5.00 g, 37.0 mmol) and cesium carbonate (14.5 g, 44.4 mmol) in dry DMF (60 ml) under nitrogen. The suspension was heated at 60 °C for 7 h. A white solid was filtered off, the yellow solution was quenched with water (5 ml) and the solvents were removed under reduced pressure. The yellow solid was partially dissolved in CHCl3 and MeOH and the insoluble material was removed by filtration. Removal of the solvents under reduced pressure resulted in a crude yellow solid that was purified by flash column chromatography (gradient, 2-10percent v/v MeOH in CHCl3). 6-Amino-9-ethyl-9H-purine was isolated as a white solid (3.97 g, 24.3 mmol, 66percent). Mp 191-194 °C (lit. 192-193 °C, 38 185-187 °C 39 ). The 1H NMR data were consistent with that in the literature. 39 1H NMR (DMSO-d6): 8.14 (s, 1H), 8.13 (s, 1H), 7.16 (br s, 2H), 4.16 (q, J 7.3 Hz, 2H), 1.39 (t, J 7.3 Hz, 3H); 13C NMR (DMSO-d6, 1): 155.9, 152.3, 149.3, 140.4, 118.8, 38.0, 15.3; νmax (DMSO) 3250, 2250, 2120, 1640 cm-1; HRMS m/z [M+H]+ calculated for C7H9N5: 164.0936. Found: 164.0935. The regioisomer (6-amino-7-ethyl-7H-purine) was also isolated as a white solid (0.60 g, 3.68 mmol, 10percent).
Reference：
[1] Tetrahedron, 2013, vol. 69, # 42, p. 8857 - 8864
[2] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 7, p. 2812 - 2822
[3] European Journal of Pharmacology, 2005, vol. 512, # 2-3, p. 157 - 164
2
[ 5324-30-1 ]
[ 66224-66-6 ]
[ 121149-94-8 ]
[ 2715-68-6 ]
Yield
Reaction Conditions
Operation in experiment
71%
With potassium carbonate In N,N-dimethyl-formamide at 153℃; for 15 h;
Potassium carbonate, 5.1 g (37 mmol), was added to a mixture of 1.8 g (7.41 mmol) of diethyl 2-bromoethylphosphonate and 1 g (7.41 mmol) of adenine in 20 mL of DMF. The mixture was refluxed for 15 h, the precipitate of potassium carbonate was filtered off, and the solvent was removed under reduced pressure. The residue was washed with acetone, and the white precipitate was filtered off and dried under reduced pressure (oil pump) until constant weight. Yield 1.6 g (71percent), mp >250°C. IR spectrum, ν,cm–1: 3143 (NH2), 1699 (C=C), 1029 (P=O). 1H NMRspectrum (DMSO-d6), δ, ppm: 1.24 t (6H, CH3, J =7.1 Hz), 2.55 d.t (2H, CH2, J = 18.2, 7.1 Hz), 4.004.09 m (4H, OCH2), 4.53 d.t (2H, CH2, J = 15.8,7.1 Hz), 8.15 s (1H, Harom), 8.24 s (1H, Harom). 31P NMR spectrum (DMSO-d6): δP 27.75 ppm. Mass spectrum: m/z 300.1 [M + H]+. Found, percent: C 44.33; H 5.81; N 23.18; P 10.54. C11H18N5O3P. Calculated, percent:C 44.15; H 6.06; N 23.40; P 10.35. M 299.3. 9-Ethyl-9H-purin-6-amine (2). The filtrate obtained after separation of compound 1 was left to stand for 12 h. The crystalline solid precipitated therefrom was filtered off and dried under reduced pressure (oil pump) until constant weight. Yield 0.1 g (9percent), mp 94-96°C. IR spectrum, ν, cm–1: 3270, 3105 (NH2), 1673 (C=C). 1H NMR spectrum (CDCl3), δ, ppm: 1.10 t(3H, CH3, J = 7.4 Hz), 3.67 q (2H, CH2, J = 7.3 Hz),7.48 s (1H, Harom), 7.53 s (1H, Harom). Mass spectrum: m/z 202 [M + K]+. Found, percent: C 51.68; H 5.70;N 43.17. C7H9N5. Calculated, percent: C 51.52; H 5.56;N 42.92. M 163.
Reference：
[1] Russian Journal of Organic Chemistry, 2018, vol. 54, # 6, p. 938 - 942[2] Zh. Org. Khim., 2018, vol. 54, # 6, p. 932 - 935,4
3
[ 74-96-4 ]
[ 66224-66-6 ]
[ 2715-68-6 ]
Reference：
[1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1983, # 12, p. 1807 - 1814
[2] Journal of the American Chemical Society, 1993, vol. 115, # 17, p. 7636 - 7644
[3] European Journal of Medicinal Chemistry, 2014, vol. 83, p. 455 - 465
4
[ 141299-24-3 ]
[ 2715-68-6 ]
Reference：
[1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1994, # 8, p. 1089 - 1098
[2] Journal of the Chemical Society - Series Chemical Communications, 1992, # 6, p. 513 - 514
5
[ 5462-86-2 ]
[ 2715-68-6 ]
Reference：
[1] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 7, p. 2812 - 2822
[2] Journal of Medicinal Chemistry, 1991, vol. 34, # 9, p. 2877 - 2882
[3] Journal of the American Chemical Society, 1957, vol. 79, p. 5238,5241
6
[ 75-03-6 ]
[ 66224-66-6 ]
[ 2715-68-6 ]
Reference：
[1] Dalton Transactions, 2015, vol. 44, # 8, p. 3540 - 3543
[2] Bioorganic and Medicinal Chemistry, 1998, vol. 6, # 5, p. 523 - 533
Reference：
[1] Journal of Organic Chemistry, 1980, vol. 45, # 20, p. 3969 - 3974
9
[ 163084-89-7 ]
[ 316352-92-8 ]
[ 2715-68-6 ]
[ 316352-98-4 ]
[ 316352-96-2 ]
Reference：
[1] Tetrahedron, 2001, vol. 57, # 30, p. 6539 - 6556
[2] Chemical Communications, 2000, # 21, p. 2131 - 2132
10
[ 141299-28-7 ]
[ 2715-68-6 ]
Reference：
[1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1994, # 8, p. 1089 - 1098
[2] Journal of the Chemical Society - Series Chemical Communications, 1992, # 6, p. 513 - 514
11
[ 66224-66-6 ]
[ 2715-68-6 ]
Reference：
[1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1994, # 8, p. 1089 - 1098
[2] Journal of the Chemical Society - Series Chemical Communications, 1992, # 6, p. 513 - 514
12
[ 98140-03-5 ]
[ 2715-68-6 ]
Reference：
[1] Journal of the American Chemical Society, 1957, vol. 79, p. 5238,5241
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