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In a glass tube 2,4-dichlorothieno[3,2-d]pyrimidine (800 mg, 3.90 mmol) was suspended in MeOH (10 mL) and cooled to −60 to −70°C upon which ammonia was bubbled in the suspension. The glass tube was sealed and the suspension stirred at room temperature overnight to obtain a clear solution. The solvent was evaporated and the resulting crude compound was purified using column chromatography eluting first with 9:1 hexanes/EtOAc, followed by 8:2 hexanes/EtOAc to obtain 6 as an off-white solid (575 mg, 3.10 mmol, 80 percent). Rf 0.2 in 3:1 hexanes/EtOAc. Mp 272.3–274.2 °C. 1H NMR (400 MHz, DMSO-d6): δ 7.73 (d, 1H, J=5.0Hz), 8.38 (br s, 2H, NH2), 8.60 (d, 1H, J=5.5Hz). 13C NMR (100 MHz, DMSO-d6): δ 114.2, 124.7, 136.6, 157.7, 160.6, 162.4. FAB-MS m/z for C6H4ClN3S calculated [M+H]+ 185.9887, found 185.9895 (35Cl), 187.9861 (37Cl).
Reference：
[1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 7, p. 2113 - 2122
2
[ 16233-51-5 ]
[ 16234-40-5 ]
Reference：
[1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 7, p. 2113 - 2122
In a glass tube 2,4-dichlorothieno[3,2-d]pyrimidine (800 mg, 3.90 mmol) was suspended in MeOH (10 mL) and cooled to -60 to -70C upon which ammonia was bubbled in the suspension. The glass tube was sealed and the suspension stirred at room temperature overnight to obtain a clear solution. The solvent was evaporated and the resulting crude compound was purified using column chromatography eluting first with 9:1 hexanes/EtOAc, followed by 8:2 hexanes/EtOAc to obtain 6 as an off-white solid (575 mg, 3.10 mmol, 80 %). Rf 0.2 in 3:1 hexanes/EtOAc. Mp 272.3-274.2 C. 1H NMR (400 MHz, DMSO-d6): delta 7.73 (d, 1H, J=5.0Hz), 8.38 (br s, 2H, NH2), 8.60 (d, 1H, J=5.5Hz). 13C NMR (100 MHz, DMSO-d6): delta 114.2, 124.7, 136.6, 157.7, 160.6, 162.4. FAB-MS m/z for C6H4ClN3S calculated [M+H]+ 185.9887, found 185.9895 (35Cl), 187.9861 (37Cl).
64%
With ammonium hydroxide; In ethanol; at 20.0℃; for 48.0h;
2,4-dichlorothieno[3,2-d]pyrimidine (51 g, 250 mmol),28% ammonia (94g, 750mmol was added to a flask containing 500mL of ethanol,The reaction was stirred for 48 hours with stirring at room temperature.TLC monitors the reaction endpoint.The precipitated solid was filtered and washed with ethanol.Drying gave Compound 28-1 (29.6 g, yield: 64%).
Compound 28-1 (29.6 g, 0.16 mol),Bromoacetophenone (34.8 g, 0.176 mol) was added to a flask containing 400 mL of DMF.The mixture was heated to 100 C with stirring for 20 hours, and TLC showed the reaction was completed.After cooling to room temperature, water was added to precipitate a solid, and the solid obtained by filtration was rinsed with ethanol.Column chromatography after dryingIt was light brownYellow solid compound 28-2 (32.8 g, 72%).
Compound 28-1 (92.5 g, 0.5 mol),Bromoacetone (81.6 g, 0.6 mmol) was added to a flask containing 700 mL of DMF.The mixture was heated to 100 C with stirring for 15 hours, and TLC showed the reaction was completed.After dropping to room temperature, water was added to precipitate a solid, and the obtained solid was filtered and washed with ethanol.Column chromatography after dryingA brownish yellow solid was obtained 30-1 (78 g, 70%).
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