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With sulfuric acid; iodine; periodic acid In water at 60℃; for 1h; Reflux; |
1a.A 6-Jodo-3H-thieno[2, 3-djpyrimklin-4-one
A 2 L round bottomed flask equipped with mechanical stirrer, thermometer and refluxcondenser was charged with the solution of 433 mL acetic acid, 13 rnL sulfuric acid and87 mL water. 69.3 g 3H-thieno[2,3-djpyrimidin-4-one (0.46 mol), 51.9 g periodic acid(0.23 mol) and 104 g iodine (0,41 mol) were added to the stirred solution heated to 60 °C for lh. The resulting suspension was cooled to room temperature, filtered off, washed with a mixture of acetic acid and water (5:1) and then with diethyl ether. The resulting beige crystalline solid was air dried.‘H NMR (500 MHz, DMSO-d6): 12.57 (brs, lH), 8.09 (s, In), 7.65 (s, 1H). |
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With iodine; periodic acid In sulfuric acid; water; acetic acid at 60℃; for 1h; |
1.A Step A: 6-Iodo-3H-thienof2, 3-dJpyrimidin-4-one
A 2 L round bottomed flask equipped with mechanical stirrer, thermometer and reflux condenser was charged with the solution of 433 mL acetic acid, 13 mL sulfuric acid and 87 mL water. 69.3 g 3H-thieno[2,3-d]pyrimidin-4-one (0.46 mol), 51.9 g periodic acid (0.23 mol) and 104 g iodine (0.41 mol) were added to the stirred solution heated to 60 °C for 1 hour. The resulting suspension was cooled to r.t., filtered off, washed with a mixture of acetic acid and water (5: 1) and then with diethyl ether. The resulting beige crystalline solid was air dried. 1H NMR (500 MHz, DMSO-d6): 12.57 (br s, 1H), 8.09 (s, 1H), 7.65 (s, 1H) |
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With sulfuric acid; iodine; acetic acid; periodic acid In water at 60℃; for 1h; |
1a.A Step A: 6-Iodo-3H-thieno[2, 3-d]pyrimidin-4-one
A 2 L round bottomed flask equipped with mechanical stirrer, thermometer and refluxcondenser was charged with the solution of 433 mL acetic acid, 13 mL sulfuric acid and87 mL water. 69.3 g 3H-thieno[2,3-d]pyrimidin-4-one (0.46 mol), 51.9 g periodic acid (0.23 mol) and 104 g iodine (0.41 mol) were added to the stirred solution, which was heated to 60 °C for 1 hour. The resulting suspension was cooled to r.t., filtered off, washed with a mixture of acetic acid and water (5:1) and then with diethyl ether. The resultingbeige crystalline solid was air dried. 1H NMR (500 MHz, DMSO-d6) ö: 12.57 (br s, 1H),8.09 (s, 1H), 7.65 (s, 1H) |
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With sulfuric acid; iodine; acetic acid; periodic acid In water at 60℃; for 1h; |
1.A Step A: 6-iodo-3H-thieno[2, 3-d]pyrimidin-4-one
A 2 L round bottomed flask equipped with mechanical stirrer, thermometer and reflux condenser was charged with the solution of 433 mL acetic acid, 13 mL sulfuric acid and 87 mL water. 69.3 g 3H-thieno[2,3-d]pyrimidin-4-one (0.46 mol), 51.9 g periodic acid (0.23 mol) and 104 g iodine (0.41 mol) were added to the stirred solution heated to 60 °C for 1 hour. The resulting suspension was cooled to r.t., filtered off, washed with a mixture of acetic acid and water (5: 1) and then with diethyl ether. The resulting beige crystalline solid was air dried to give 6-iodo-3H-thieno[2,3-d]pyrimidin-4-one. 1H NMR (500 MHz, DMSO-de) δ 12.57 (br s, 1H), 8.09 (s, 1H), 7.65 (s, 1H) (0235) 13C NMR (125 MHz, DMSO-d6) δ 168.3, 155.9, 146.1, 130.8, 126.7, 76.4 |
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With sulfuric acid; iodine; periodic acid In acetic acid at 60℃; for 1h; |
8.A Step A: 6-Iodo-3H-thienof2, 3-dJpyrimidin-4-one
Step A: 6-Iodo-3H-thienof2, 3-dJpyrimidin-4-one (0168) A 2 L round bottomed flask equipped with mechanical stirrer, thermometer and reflux condenser was charged with the solution of 433 mL acetic acid, 13 mL sulfuric acid and 87 mL water. 69.3 g 3H-thieno[2,3-d]pyrimidin-4-one (0.46 mol), 51.9 g periodic acid (0.23 mol) and 104 g iodine (0.41 mol) were added to the stirred solution, which was heated to 60 °C for 1 hour. The resulting suspension was cooled to room temperature, filtered off, washed with a mixture of acetic acid and water (5 : 1) and then with diethyl ether. The resulting beige crystalline solid was air dried. 1H NMR (500 MHz, DMSO-d6) δ: 12.57 (br s, 1H), 8.09 (s, 1H), 7.65 (s, 1H) |
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With sulfuric acid; iodine; acetic acid; periodic acid In water at 70℃; for 0.75h; |
1.1I 6-iodothieno[2,3-d]pyrimidin-4(3H)-one
Acetic acid (312 mL), sulfuric acid (9.37 mL) and water (63 mL) were combined with stirring. Thieno[2,3-cT|pyrimidin-4(3 /)-one (50 g), periodic acid (37.4 g) and iodine (75 g) were added sequentially, and the mixture was slightly endothermic. A heating mantle was added and the reaction mixture was ramped up to 60 °C. Midway through, the temperature climbed to 68-69 °C. The heating mantle was removed and the temperature was maintained at 70 °C by self-heating for about 45 minutes. LC/MS indicated a single peak corresponding to desired product. The reaction mixture was cooled to room temperature. The resulting suspension was filtered, washed with 5 : 1 acetic acid:water (three times) and diethyl ether (five times) to provide the title compound which was used in the next step without further purification. NMR (400 MHz, DMSO-6) δ ppm 12.80-12.41 (m, 1H), 8.10 (s, 1H), 7.66 (s, 1H). MS (ESI) m/z 277.9 (M-H)- |
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With sulfuric acid; iodine; acetic acid; periodic acid In water at 60 - 70℃; |
1.1A 6-iodothieno[2,3-d]pyrimidin-4(3H)-one
Example 1A 6-iodothieno[2,3-d]pyrimidin-4(3H)-one Acetic acid (312 mL), sulfuric acid (9.37 mL) and water (63 mL) were combined with stirring. Thieno[2,3-d]pyrimidin-4(3H)-one (50 g), periodic acid (37.4 g) and iodine (75 g) were added sequentially, and the mixture became slightly endothermic. A heating mantle was added and the reaction mixture was ramped up to 60° C. Midway through, the temperature climbed to 68-69° C. The heating mantle was removed and the temperature was maintained at 70° C. by self-heating for about 45 minutes. LC/MS indicated a single peak corresponding to the title compound. The reaction mixture was cooled to room temperature. The resulting suspension was filtered, and washed with 5:1 acetic acid:water (three times), and diethyl ether (5*) to provide the title compound which was used in the next step without further purification. 1H NMR (400 MHz, dimethyl sulfoxide-d6) δ ppm 12.80-12.41 (m, 1H), 8.10 (s, 1H), 7.66 (s, 1H). MS (ESI) m/z 277.9 (M-H)-. |
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With sulfuric acid; iodine; acetic acid; periodic acid In water at 60 - 70℃; for 0.75h; |
4A Example 4A6-iodothieno[2,3-djpyrimidin-4(3R)-one
Acetic acid (312 mL), sulfuric acid (9.37 mL) and water (63 mL) were combined with stirring. Thieno[2,3-djpyrimidin-4(3H)-one (50 g), periodic acid (37.4 g) and iodine (75 g) were addedsequentially, and the mixture became slightly endothermic. A heating mantle was added and the reaction mixture was ramped up to 60 °C. Midway through, the temperature climbed to 68-69 °C. The heating mantle was removed and the temperature was maintained at 70 °C by self-heating for about 45 minutes. The reaction mixture was cooled to room temperature. The resulting suspension was filtered, washed with 5:1 acetic acid:water (three times), and washed with diethyl ether (five times) to provide the titlecompound which was used in the next step without further purification. ‘H NMR (400 MHz, dimethylsulfoxide-d6) 6 ppm 12.80-12.41 (m, 1H), 8.10 (s, 111), 7.66 (s, IH). MS (ESI) m/z 277.9 (MH). |
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