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CAS No. : | 175137-13-0 | MDL No. : | MFCD00205194 |
Formula : | C7H6N2OS | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KJTYNZWEAIRZHT-UHFFFAOYSA-N |
M.W : | 166.20 | Pubchem ID : | 135439636 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 | UN#: | |
Hazard Statements: | H302-H312-H315-H319-H332-H335 | Packing Group: | |
GHS Pictogram: |
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* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | for 2 h; Heating / reflux | 4-Chloro-7-methylthieno[3,2-d]pyrimidine (168): A solution of 7-methyl-3H-thieno[3,2-d]pyrimid-4-one (167, 10.6 g, 64.0 mmol) in phosphorus oxychloride (42 mL) was refluxed under N2 for 2 hours. The resulting solution was allowed to cool to room temperature and then neutralized by carefully pouring into a saturated aqueous solution of sodium carbonate (300 mL). The aqueous mixture was extracted with ethyl acetate and the organic layer washed with water and brine, before drying over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue dried over P2O5 under vacuum overnight (11.2 g, 95percent yield, white solid). |
81% | With trichlorophosphate In N,N-dimethyl-formamide at 110℃; for 4 h; | 7-methyl-3H-thieno[3,2-d]pyrimidin-4-one (9 g, 54.2 mmol), DMF (lmL), POCl3 (80mL) were mixed and refluxed for 4 hours at 110°C. The reaction solution was cooled to room temperature, and the reaction mixture was concentrated under reduced pressure. The reaction mixture was added with toluene, and further concentrated under reduced pressure. The resulting residue was neutralized with sodium bicarbonate, subjected to extraction with ethyl acetate, dried, and filtered to obtain the title compound (8.1 g, 81percent). -NMR Spectrum (300 MHz, CDC13): δ 9.01 (s, IH), 7.69 (s, IH), 2.53 (s, 3H) |
81% | at 110℃; for 4 h; | 7-methyl-3H-thieno[3,2-d]pyrimidin-4-one (9 g, 54.2 mmol), DMF (1 mL), POCl3 (80 mL) were mixed and refluxed for 4 hours at 110° C. The reaction solution was cooled to room temperature, and the reaction mixture was concentrated under reduced pressure. The reaction mixture was added with toluene, and further concentrated under reduced pressure. The resulting residue was neutralized with sodium bicarbonate, subjected to extraction with ethyl acetate, dried, and filtered to obtain the title compound (8.1 g, 81percent). 1H-NMR Spectrum (300 MHz, CDCl3): δ 9.01 (s, 1H), 7.69 (s, 1H), 2.53 (s, 3H) |
20% | for 3 h; Reflux | Synthesis of intermediate XI 11-011-07 XIII-01A mixture of Intermediate 1-07 (4.85 g, 24.34 mnmol) and POCI3 (20 mL) was refluxed for 3 h. On cooling, the solvents were removed in vacuo, the residue was suspended in water and the suspension was cooled to 0 °C. Aqueous saturated Na2C03 was added dropwise at 0 °C up to pH~8. The resulting solid was filtered, washed with water and dried to give Intermediate XIII-01 (1.1 g, 20percent) as a white solid. H NMR (300 MHz, DMSO) δ 9.01 (s, 1H), 8.19 (q, J = 1.1 Hz, 1H), 2.39 (d, J = 1.1 Hz, 3H). |
1.9 g | at 100℃; for 6 h; | Commercially available methyl 3-amino-4-methylthiophene-2-carboxylate 13 (16.5 g, 96.0 mmol) was dissolved in formamide (100 mL) and stirred at 150 °C under nitrogen atmosphere. After the starting material consumption had been confirmed by LC-MS, the reaction mixture was cooled to room temperature and then H2O (500 mL) was added to the mixture. The suspension was filtered to collect a white solid that was dried by an oil pump to give 7-methylthieno[3,2-d]pyrimidin-4(3H)-one (12.2 g). The solid was used for the next reaction without further purification. The aforementioned 7-methylthieno[3,2-d]pyrimidin-4(3H)-one (1.85 g) was treated with POCl3 (8.80 mL) and stirred at 100 °C for 6 h. The reaction mixture was cooled to 0 °C, poured into ice-water/ethyl acetate, and extracted with ethyl acetate twice. The organic layer was washed with brine, dried over Na2SO4, and filtered. The organic solvent was concentrated under reduced pressure to give a crude residue. Water (200 mL) was added to the residue and the mixture cooled at 5 °C in the refrigerator for a day. The suspension was filtered to afford 14 (1.90 g, 2 steps 72percent) as a white solid. 1H NMR (400 MHz, DMSO-D6) δ: 9.07 (1H, s), 8.25 (1H, d, J = 1.2 Hz), 2.45 (3H, d, J = 1.2 Hz). 13C NMR (100 MHz, DMSO-D6) δ: 160.7, 153.9, 153.6, 133.9, 133.2, 130.0, 12.5. HRMS (ESI-TOF) m/z: [M+H]+ Calcd for C7H6ClN2S 184.9940; Found 184.9937. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With sodium hydrogencarbonate In trichlorophosphate | A solution of 7-methyl-3H-thieno[3,2-d]pyrimid-4-one (3, 2.9 g, 18 mmol) in phosphorus oxychloride (18 mL) under N2 was heated at reflux for 1 hour. The resulting solution was allowed to cool to room temperature and then poured into a saturated aqueous solution of sodium bicarbonate to neutralize. The aqueous mixture was extracted with diethyl ether. The organic layer was washed with water followed by saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and the solvent evaporated under reduced pressure to yield 4-chloro-7-methylthieno[3,2-d]pyrimidine (3.1 g, 96percent yield) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With ammonium formate In formamide | To a solution of ammonium formate (5.1 g, 81 mmol) in formamide (25 mL) at 150° C. was added 3-(formylamino)-4-methyl-2-thiophenecarboxylic acid methyl ester (2, 5.0 g, 25 mmol) as a solid in small portions. The resulting solution was heated at 150° C. for 5 hours and then allowed to stand at room temperature for 12 hours. The precipitate that formed was collected by vacuum filtration to give 7-methyl-3H-thieno[3,2-d]pyrimid-4-one (3.4 g, 84percent yield) as white needles. 4-Chloro-7-methylthieno[3,2-d]pyrimidine (4). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With trichlorophosphate; for 2h;Heating / reflux; | 4-Chloro-7-methylthieno[3,2-d]pyrimidine (168): A solution of 7-methyl-3H-thieno[3,2-d]pyrimid-4-one (167, 10.6 g, 64.0 mmol) in phosphorus oxychloride (42 mL) was refluxed under N2 for 2 hours. The resulting solution was allowed to cool to room temperature and then neutralized by carefully pouring into a saturated aqueous solution of sodium carbonate (300 mL). The aqueous mixture was extracted with ethyl acetate and the organic layer washed with water and brine, before drying over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue dried over P2O5 under vacuum overnight (11.2 g, 95% yield, white solid). |
81% | With trichlorophosphate; In N,N-dimethyl-formamide; at 110℃; for 4h; | 7-methyl-3H-thieno[3,2-d]pyrimidin-4-one (9 g, 54.2 mmol), DMF (lmL), POCl3 (80mL) were mixed and refluxed for 4 hours at 110C. The reaction solution was cooled to room temperature, and the reaction mixture was concentrated under reduced pressure. The reaction mixture was added with toluene, and further concentrated under reduced pressure. The resulting residue was neutralized with sodium bicarbonate, subjected to extraction with ethyl acetate, dried, and filtered to obtain the title compound (8.1 g, 81%). -NMR Spectrum (300 MHz, CDC13): δ 9.01 (s, IH), 7.69 (s, IH), 2.53 (s, 3H) |
81% | With N,N-dimethyl-formamide; trichlorophosphate; at 110℃; for 4h; | 7-methyl-3H-thieno[3,2-d]pyrimidin-4-one (9 g, 54.2 mmol), DMF (1 mL), POCl3 (80 mL) were mixed and refluxed for 4 hours at 110 C. The reaction solution was cooled to room temperature, and the reaction mixture was concentrated under reduced pressure. The reaction mixture was added with toluene, and further concentrated under reduced pressure. The resulting residue was neutralized with sodium bicarbonate, subjected to extraction with ethyl acetate, dried, and filtered to obtain the title compound (8.1 g, 81%). 1H-NMR Spectrum (300 MHz, CDCl3): δ 9.01 (s, 1H), 7.69 (s, 1H), 2.53 (s, 3H) |
20% | With trichlorophosphate; for 3h;Reflux; | Synthesis of intermediate XI 11-011-07 XIII-01A mixture of Intermediate 1-07 (4.85 g, 24.34 mnmol) and POCI3 (20 mL) was refluxed for 3 h. On cooling, the solvents were removed in vacuo, the residue was suspended in water and the suspension was cooled to 0 C. Aqueous saturated Na2C03 was added dropwise at 0 C up to pH~8. The resulting solid was filtered, washed with water and dried to give Intermediate XIII-01 (1.1 g, 20%) as a white solid. H NMR (300 MHz, DMSO) δ 9.01 (s, 1H), 8.19 (q, J = 1.1 Hz, 1H), 2.39 (d, J = 1.1 Hz, 3H). |
7-Methylthieno[3,2-d]pyrimidine-4(3H)-one (1.5g) was added to POCl3 (lOmL), and the mixture was stirred at 110C for 2 hours. The reaction mixture was cooled to room temperature, concentrated and dilluted with DCM, and sat. NaHC03 solution was added thereto. The aqueous layer was extracted with DCM to combine organic layers. The organic layer was dried with MgS04 and filtered to obtain the title compound as a white solid.1H NMR (400MHz, DMSO-d6) δ 9.06 (s, 1H), 8.24 (s, 1H), 2.43 (s, 3H). | ||
7-Methylthieno[3,2-d]pyrimidine-4(3H)-one(1.5g) was dissolved in phosphorous oxychloride(lOmL) and stirred at 110 C for 2 hrs. The reaction mixture was cooled to room temperature and concentrated under a reduced pressure. The resulting concentrate was added to a mixture of dichloromethane and a saturated sodium bicarbonate solution. The aqueous layer was extracted with dichloromethane four times. The combined organic layers were dried over magnesium sulfate and concentrated under a reduced pressure to obtain the title compound as a cream and white solid.1H NMR (400MHz, DMSO-d6) δ 9.06(s, 1H), 8.24 (s, 1H), 2.43(s, 3H). | ||
With trichlorophosphate; at 100℃; for 1h; | A suspension of 7-methyl-3H-thieno[3,2-d]pyrimidin-4-one (2.1 g) in phosphorus oxychloride (10 mL) was heated at 100 C. for 1 hour. The reaction mixture was then cooled and poured into a mixture of ice-water and ethyl acetate. The organic layer was separated, washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography (DCM) to afford 2.0 g of 4-chloro-7-methyl-thieno[3,2-d]pyrimidine. | |
With trichlorophosphate; at 110℃; for 2h; | b. 4-Chloro-7-methylthieno[3,2-d]pyrimidine 7-Methylthieno[3,2-d]pyrimidine-4(3H)-one (1.5 g) was dissolved in phosphorous oxychloride (10 mL) and stirred at 110 C. for 2 hrs. The reaction mixture was cooled to room temperature and concentrated under a reduced pressure. The resulting concentrate was added to a mixture of dichloromethane and a saturated sodium bicarbonate solution. The aqueous layer was extracted with dichloromethane four times. The combined organic layers were dried over magnesium sulfate and concentrated under a reduced pressure to obtain the title compound as a cream and white solid. 1H NMR (400 MHz, DMSO-d6) δ 9.06 (s, 1H), 8.24 (s, 1H), 2.43 (s, 3H). | |
With trichlorophosphate; at 110℃; for 2h; | Step 2: 4-Chloro-7-methylthieno[3,2-d]pyrimidine 7-Methylthieno[3,2-d]pyrimidine-4(3H)-one (1.5 g) was added to POCl3 (10 mL), and the mixture was stirred at 110 C. for 2 hours. The reaction mixture was cooled to room temperature, concentrated and diluted with DCM, and sat. NaHCO3 solution was added thereto. The aqueous layer was extracted with DCM to combine organic layers. The organic layer was dried with MgSO4 and filtered to obtain the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 9.06 (s, 1H), 8.24 (s, 1H), 2.43 (s, 3H). | |
1.9 g | With trichlorophosphate; at 100℃; for 6h; | Commercially available methyl 3-amino-4-methylthiophene-2-carboxylate 13 (16.5 g, 96.0 mmol) was dissolved in formamide (100 mL) and stirred at 150 C under nitrogen atmosphere. After the starting material consumption had been confirmed by LC-MS, the reaction mixture was cooled to room temperature and then H2O (500 mL) was added to the mixture. The suspension was filtered to collect a white solid that was dried by an oil pump to give 7-methylthieno[3,2-d]pyrimidin-4(3H)-one (12.2 g). The solid was used for the next reaction without further purification. The aforementioned 7-methylthieno[3,2-d]pyrimidin-4(3H)-one (1.85 g) was treated with POCl3 (8.80 mL) and stirred at 100 C for 6 h. The reaction mixture was cooled to 0 C, poured into ice-water/ethyl acetate, and extracted with ethyl acetate twice. The organic layer was washed with brine, dried over Na2SO4, and filtered. The organic solvent was concentrated under reduced pressure to give a crude residue. Water (200 mL) was added to the residue and the mixture cooled at 5 C in the refrigerator for a day. The suspension was filtered to afford 14 (1.90 g, 2 steps 72%) as a white solid. 1H NMR (400 MHz, DMSO-D6) δ: 9.07 (1H, s), 8.25 (1H, d, J = 1.2 Hz), 2.45 (3H, d, J = 1.2 Hz). 13C NMR (100 MHz, DMSO-D6) δ: 160.7, 153.9, 153.6, 133.9, 133.2, 130.0, 12.5. HRMS (ESI-TOF) m/z: [M+H]+ Calcd for C7H6ClN2S 184.9940; Found 184.9937. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | Stage #1: methyl 3-formamido-4-methylthiophene-2-carboxylate With ammonium formate In formamide at 160℃; for 18h; Stage #2: for 0.5h; | Synthesis of Intermediate 1-07A mixture of Intermediate 1-06 (4.65 g, 23.25 mmol) and ammonium formate (10 g, 200 mmol) in formamide (6 mL) was heated at 160 °C for 18 h. On cooling, the resulting solid was filtered, washed with acetone and dried to give Intermediate 1- 07 (3.85 g, 99%) as a white solid.1H N R (300 MHz, DMSO) δ 8.18 (s, 1H), 7.81 (d, J = 0.7 Hz, 1H), 2.31 (d, J = 0.9 Hz, 3H). |
72% | With ammonium formate In formamide at 160℃; for 6h; | 1; 2; 3; 4; 5 7-Methyl-3H-thieno[3,2-d]pyrimid-4-one (167): 3-(Formylamino)-4-methyl-2-thiophenecarboxylic acid methyl ester (166, 10.0 g, 50.0 mmol), ammonium formate 26.0 g, (400 mmol) and formamide (12 mL) were heated at 160° C. for 6 hours under N2 and then cooled to room temperature. The precipitate was collected by vacuum filtration, washed with acetone, and dried over P2O5 under vacuum overnight (6.0 g 72% yield, white needles). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With sodium hydrogencarbonate; In trichlorophosphate; | A solution of 7-methyl-3H-thieno[3,2-d]pyrimid-4-one (3, 2.9 g, 18 mmol) in phosphorus oxychloride (18 mL) under N2 was heated at reflux for 1 hour. The resulting solution was allowed to cool to room temperature and then poured into a saturated aqueous solution of sodium bicarbonate to neutralize. The aqueous mixture was extracted with diethyl ether. The organic layer was washed with water followed by saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and the solvent evaporated under reduced pressure to yield 4-chloro-7-methylthieno[3,2-d]pyrimidine (3.1 g, 96% yield) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With ammonium formate; In formamide; | To a solution of ammonium formate (5.1 g, 81 mmol) in formamide (25 mL) at 150 C. was added 3-(formylamino)-4-methyl-2-thiophenecarboxylic acid methyl ester (2, 5.0 g, 25 mmol) as a solid in small portions. The resulting solution was heated at 150 C. for 5 hours and then allowed to stand at room temperature for 12 hours. The precipitate that formed was collected by vacuum filtration to give 7-methyl-3H-thieno[3,2-d]pyrimid-4-one (3.4 g, 84% yield) as white needles. 4-Chloro-7-methylthieno[3,2-d]pyrimidine (4). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | at 200℃; for 24h; | 58.1 Preparation of 7-methyl-3H-thieno[3,2-d]pyrimidin-4-one 3- amino-4-methyl-thiophene-2-carboxylic acid methyl ester (10.2 g, 59.6 mmol) was dissolved in formamide (25 mL), followed by refluxing for 24 hours at 200°C. The reaction solution was slowly cooled to room temperature. The resulting solid was filtered, washed with diethyl ether, and dried to obtain the title compound (9 g, 91%). 1H-NMR Spectrum (300 MHz, DMSO-i): δ 8.17 (s, IH), 7.81 (s, IH), 2.31 (s, 3H) |
91% | at 200℃; for 24h; | 58.1 Preparation of 7-methyl-3H-thieno[3,2-d]pyrimidin-4-one 3-amino-4-methyl-thiophene-2-carboxylic acid methyl ester (10.2 g, 59.6 mmol) was dissolved in formamide (25 mL), followed by refluxing for 24 hours at 200° C. The reaction solution was slowly cooled to room temperature. The resulting solid was filtered, washed with diethyl ether, and dried to obtain the title compound (9 g, 91%). 1H-NMR Spectrum (300 MHz, DMSO-d6): δ 8.17 (s, 1H), 7.81 (s, 1H), 2.31 (s, 3H) |
60% | at 20℃; |
at 200℃; for 3h; | 7; 3.1 Methyl 3-amino-4-methylthiophene-2-carboxylate (3.0g) was added to formamide (5mL), and the mixture was stirred at 200°C for 3 hours. After cooling to room temperature water (50mL) was added thereto and then stirred for 15 hours at room temperature to obtain a solid. The solid was filtered, washed with water and dried with N2 gas to obtain the title compound as a white solid without further purification.1H NMR (400MHz, DMSO-d6) δ 12.50 (br, 1H), 8.16 (s, 1H), 7.86 (s, 1H), 2.30 (s,3H). | |
at 200℃; for 3h; | 7; 107.a Methyl 3-amino-4-methylthiophene-2-carboxylate(3.0g) (Aldrich, Catalog No. 546658) was dissolved in formamide(5mL), stirred at 200 °C for 3 hrs, and cooled to room temperature. Water(50mL) was added thereto, which was stirred at room temperature for 15 hrs. The resulting solution was filtered, and the solid thus obtained was washed with water and dried. The solid was added to acetone/diethyl ether, which was stirred and filtered to obtain the title compound as a white solid. NMR (400MHz, DMSO-d6) δ 12.50 (br, 1H), 8.16(s, 1H), 7.86 (s, 1H),2.30(s, 3H). | |
at 150℃; | 12.A A mixture of 3-amino-4-methyl-thiophene-2-carboxylic acid methyl ester (3.0 g) and formamide (50 mL) was heated to 150° C. overnight. The reaction mixture was then cooled and diluted with water. The solid formed was collected by filtration, washed with water and dried under reduced pressure to give 2.1 g of 7-methyl-3H-thieno[3,2-d]pyrimidin-4-one without further purifications. | |
at 200℃; for 3h; | 107.a a. 7-Methylthieno[3,2-d]pyrimidin-4(3H)-one Methyl 3-amino-4-methylthiophene-2-carboxylate (3.0 g) (Aldrich, Catalog No. 546658) was dissolved in formamide (5 mL), stirred at 200° C. for 3 hrs, and cooled to room temperature. Water (50 mL) was added thereto, which was stirred at room temperature for 15 hrs. The resulting solution was filtered, and the solid thus obtained was washed with water and dried. The solid was added to acetone/diethyl ether, which was stirred and filtered to obtain the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 12.50 (br, 1H), 8.16 (s, 1H), 7.86 (s, 1H), 2.30 (s, 3H). | |
Stage #1: formamide; 3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester In water at 200℃; for 3h; Stage #2: In water at 20℃; for 15h; | P.3.1 Step 1: 7-Methylthieno[3,2-d]pyrimidine-4(3H)-one Methyl 3-amino-4-methylthiophene-2-carboxylate (3.0 g) was added to formamide (5 mL), and the mixture was stirred at 200° C. for 3 hours. After cooling to room temperature water (50 mL) was added thereto and then stirred for 15 hours at room temperature to obtain a solid. The solid was filtered, washed with water and dried with N2 gas to obtain the title compound as a white solid without further purification. 1H NMR (400 MHz, DMSO-d6) δ 12.50 (br, 1H), 8.16 (s, 1H), 7.86 (s, 1H), 2.30 (s, 3H). | |
12.2 g | at 150℃; Inert atmosphere; | Commercially available methyl 3-amino-4-methylthiophene-2-carboxylate 13 (16.5 g, 96.0 mmol) was dissolved in formamide(100 mL) and stirred at 150°C under nitrogen atmosphere. After the starting material consumption had been confirmed by LC-MS, the reaction mixture was cooled to room temperature and then H2O (500 mL) was added to the mixture. The suspension was filtered to collect a white solid that was dried by an oil pump to give 7-methylthieno[3,2-d]pyrimidin-4(3H)-one (12.2 g). The solid was used for the next reaction without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: trichlorophosphate / 2 h / 110 °C 2: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 1 h / 100 °C | ||
Multi-step reaction with 2 steps 1: trichlorophosphate / 2 h / 110 °C 2: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: trichlorophosphate / 2 h / 110 °C 2: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 1 h / 100 °C 3: potassium iodide / N,N-dimethyl-formamide / 4 h / 35 °C 4: sodium hydroxide / tetrahydrofuran / 0.5 h / 20 °C 5: manganese(IV) oxide / chloroform / 2 h / 70 °C 6: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; dimethyl sulfoxide / 0 - 20 °C | ||
Multi-step reaction with 6 steps 1: trichlorophosphate / 2 h / 110 °C 2: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 100 °C 3: potassium iodide / N,N-dimethyl-formamide / 4 h / 35 °C 4: water; sodium hydroxide / tetrahydrofuran / 0.5 h 5: manganese(IV) oxide / chloroform / 2 h / 70 °C 6: sodium dihydrogenphosphate dihydrate; sodium chlorite / water; dimethyl sulfoxide / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: trichlorophosphate / 2 h / 110 °C 2: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 1 h / 100 °C 3: potassium iodide / N,N-dimethyl-formamide / 4 h / 35 °C | ||
Multi-step reaction with 3 steps 1: trichlorophosphate / 2 h / 110 °C 2: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 100 °C 3: potassium iodide / N,N-dimethyl-formamide / 4 h / 35 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: trichlorophosphate / 2 h / 110 °C 2: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 1 h / 100 °C 3: potassium iodide / N,N-dimethyl-formamide / 4 h / 35 °C 4: sodium hydroxide / tetrahydrofuran / 0.5 h / 20 °C | ||
Multi-step reaction with 4 steps 1: trichlorophosphate / 2 h / 110 °C 2: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 100 °C 3: potassium iodide / N,N-dimethyl-formamide / 4 h / 35 °C 4: water; sodium hydroxide / tetrahydrofuran / 0.5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: trichlorophosphate / 2 h / 110 °C 2: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 1 h / 100 °C 3: potassium iodide / N,N-dimethyl-formamide / 4 h / 35 °C 4: sodium hydroxide / tetrahydrofuran / 0.5 h / 20 °C 5: manganese(IV) oxide / chloroform / 2 h / 70 °C | ||
Multi-step reaction with 5 steps 1: trichlorophosphate / 2 h / 110 °C 2: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 100 °C 3: potassium iodide / N,N-dimethyl-formamide / 4 h / 35 °C 4: water; sodium hydroxide / tetrahydrofuran / 0.5 h 5: manganese(IV) oxide / chloroform / 2 h / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: trichlorophosphate / 2 h / 110 °C 2: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 1 h / 100 °C 3: potassium iodide / N,N-dimethyl-formamide / 4 h / 35 °C 4: sodium hydroxide / tetrahydrofuran / 0.5 h / 20 °C 5: manganese(IV) oxide / chloroform / 2 h / 70 °C 6: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; dimethyl sulfoxide / 0 - 20 °C 7: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / acetonitrile / 15 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1: trichlorophosphate / 2 h / 110 °C 2: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 1 h / 100 °C 3: potassium iodide / N,N-dimethyl-formamide / 4 h / 35 °C 4: sodium hydroxide / tetrahydrofuran / 0.5 h / 20 °C 5: manganese(IV) oxide / chloroform / 2 h / 70 °C 6: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; dimethyl sulfoxide / 0 - 20 °C 7: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / acetonitrile / 15 h / 20 °C 8: ammonia / isopropyl alcohol / 10 h / 70 °C / closed vessel | ||
Multi-step reaction with 8 steps 1: trichlorophosphate / 2 h / 110 °C 2: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 1 h / 100 °C 3: potassium iodide / N,N-dimethyl-formamide / 4 h / 35 °C 4: sodium hydroxide / tetrahydrofuran / 0.5 h / 20 °C 5: manganese(IV) oxide / chloroform / 2 h / 70 °C 6: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; dimethyl sulfoxide / 0 - 20 °C 7: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / acetonitrile / 15 h / 20 °C 8: ammonia / isopropyl alcohol / 10 h / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 9 steps 1: trichlorophosphate / 2 h / 110 °C 2: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 1 h / 100 °C 3: potassium iodide / N,N-dimethyl-formamide / 4 h / 35 °C 4: sodium hydroxide / tetrahydrofuran / 0.5 h / 20 °C 5: manganese(IV) oxide / chloroform / 2 h / 70 °C 6: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; dimethyl sulfoxide / 0 - 20 °C 7: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / acetonitrile / 15 h / 20 °C 8: ammonia / isopropyl alcohol / 10 h / 70 °C / closed vessel 9: isopropyl alcohol / 15 h / 110 °C | ||
Multi-step reaction with 8 steps 1: trichlorophosphate / 2 h / 110 °C 2: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 1 h / 100 °C 3: potassium iodide / N,N-dimethyl-formamide / 4 h / 35 °C 4: sodium hydroxide / tetrahydrofuran / 0.5 h / 20 °C 5: manganese(IV) oxide / chloroform / 2 h / 70 °C 6: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; dimethyl sulfoxide / 0 - 20 °C 7: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / acetonitrile / 15 h / 20 °C 8: isopropyl alcohol / 15 h / 110 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: trichlorophosphate / 2 h / 110 °C 2: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 1 h / 100 °C 3: potassium iodide / N,N-dimethyl-formamide / 4 h / 35 °C 4: sodium hydroxide / tetrahydrofuran / 0.5 h / 20 °C 5: manganese(IV) oxide / chloroform / 2 h / 70 °C 6: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; dimethyl sulfoxide / 0 - 20 °C 7: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / acetonitrile / 15 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1.1: trichlorophosphate / 2 h / 110 °C 2.1: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 1 h / 100 °C 3.1: potassium iodide / N,N-dimethyl-formamide / 4 h / 35 °C 4.1: sodium hydroxide / tetrahydrofuran / 0.5 h / 20 °C 5.1: manganese(IV) oxide / chloroform / 2 h / 70 °C 6.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; dimethyl sulfoxide / 0 - 20 °C 7.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / acetonitrile / 15 h / 20 °C 8.1: sulfuryl dichloride / dichloromethane; acetonitrile / 1 h / 0 - 20 °C 8.2: pH 8 | ||
Multi-step reaction with 8 steps 1: trichlorophosphate / 2 h / 110 °C 2: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 1 h / 100 °C 3: potassium iodide / N,N-dimethyl-formamide / 4 h / 35 °C 4: sodium hydroxide / tetrahydrofuran / 0.5 h / 20 °C 5: manganese(IV) oxide / chloroform / 2 h / 70 °C 6: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; dimethyl sulfoxide / 0 - 20 °C 7: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / acetonitrile / 15 h / 20 °C 8: sulfuryl dichloride / dichloromethane; acetonitrile / 1 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 9 steps 1.1: trichlorophosphate / 2 h / 110 °C 2.1: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 1 h / 100 °C 3.1: potassium iodide / N,N-dimethyl-formamide / 4 h / 35 °C 4.1: sodium hydroxide / tetrahydrofuran / 0.5 h / 20 °C 5.1: manganese(IV) oxide / chloroform / 2 h / 70 °C 6.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; dimethyl sulfoxide / 0 - 20 °C 7.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / acetonitrile / 15 h / 20 °C 8.1: sulfuryl dichloride / dichloromethane; acetonitrile / 1 h / 0 - 20 °C 8.2: pH 8 9.1: caesium carbonate / 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 2.5 h / 120 °C | ||
Multi-step reaction with 9 steps 1: trichlorophosphate / 2 h / 110 °C 2: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 1 h / 100 °C 3: potassium iodide / N,N-dimethyl-formamide / 4 h / 35 °C 4: sodium hydroxide / tetrahydrofuran / 0.5 h / 20 °C 5: manganese(IV) oxide / chloroform / 2 h / 70 °C 6: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; dimethyl sulfoxide / 0 - 20 °C 7: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / acetonitrile / 15 h / 20 °C 8: sulfuryl dichloride / dichloromethane; acetonitrile / 1 h / 0 - 20 °C 9: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 2.5 h / 120 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1.1: trichlorophosphate / 2 h / 110 °C 2.1: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 1 h / 100 °C 3.1: potassium iodide / N,N-dimethyl-formamide / 4 h / 35 °C 4.1: sodium hydroxide / tetrahydrofuran / 0.5 h / 20 °C 5.1: isopropyl alcohol / 12 h / Reflux 6.1: manganese(IV) oxide / chloroform / 12 °C / Reflux 7.1: sodium dihydrogenphosphate dihydrate / water; dimethyl sulfoxide; acetone / 0.5 h / 0 °C 7.2: 0 - 20 °C 8.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.25 h / 20 °C 8.2: 16 h / 45 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1.1: trichlorophosphate / 2 h / 110 °C 2.1: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 1 h / 100 °C 3.1: potassium iodide / N,N-dimethyl-formamide / 4 h / 35 °C 4.1: sodium hydroxide / tetrahydrofuran / 0.5 h / 20 °C 5.1: isopropyl alcohol / 12 h / Reflux 6.1: manganese(IV) oxide / chloroform / 12 °C / Reflux 7.1: sodium dihydrogenphosphate dihydrate / water; dimethyl sulfoxide; acetone / 0.5 h / 0 °C 7.2: 0 - 20 °C 8.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.5 h / 20 °C 8.2: 17 h / 45 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1.1: trichlorophosphate / 2 h / 110 °C 2.1: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 1 h / 100 °C 3.1: potassium iodide / N,N-dimethyl-formamide / 4 h / 35 °C 4.1: sodium hydroxide / tetrahydrofuran / 0.5 h / 20 °C 5.1: isopropyl alcohol / 12 h / Reflux 6.1: manganese(IV) oxide / chloroform / 12 °C / Reflux 7.1: sodium dihydrogenphosphate dihydrate / water; dimethyl sulfoxide; acetone / 0.5 h / 0 °C 7.2: 0 - 20 °C 8.1: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 24 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 9 steps 1.1: trichlorophosphate / 2 h / 110 °C 2.1: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 1 h / 100 °C 3.1: potassium iodide / N,N-dimethyl-formamide / 4 h / 35 °C 4.1: sodium hydroxide / tetrahydrofuran / 0.5 h / 20 °C 5.1: isopropyl alcohol / 12 h / Reflux 6.1: manganese(IV) oxide / chloroform / 12 °C / Reflux 7.1: sodium dihydrogenphosphate dihydrate / water; dimethyl sulfoxide; acetone / 0.5 h / 0 °C 7.2: 0 - 20 °C 8.1: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 24 h / 20 °C 9.1: trifluoroacetic acid / dichloromethane / 8 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: trichlorophosphate / 2 h / 110 °C 2: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 1 h / 100 °C 3: potassium iodide / N,N-dimethyl-formamide / 4 h / 35 °C 4: sodium hydroxide / tetrahydrofuran / 0.5 h / 20 °C 5: isopropyl alcohol / 12 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: trichlorophosphate / 2 h / 110 °C 2: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 1 h / 100 °C 3: potassium iodide / N,N-dimethyl-formamide / 4 h / 35 °C 4: sodium hydroxide / tetrahydrofuran / 0.5 h / 20 °C 5: isopropyl alcohol / 12 h / Reflux 6: manganese(IV) oxide / chloroform / 12 °C / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: trichlorophosphate / 2 h / 110 °C 2.1: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 1 h / 100 °C 3.1: potassium iodide / N,N-dimethyl-formamide / 4 h / 35 °C 4.1: sodium hydroxide / tetrahydrofuran / 0.5 h / 20 °C 5.1: isopropyl alcohol / 12 h / Reflux 6.1: manganese(IV) oxide / chloroform / 12 °C / Reflux 7.1: sodium dihydrogenphosphate dihydrate / water; dimethyl sulfoxide; acetone / 0.5 h / 0 °C 7.2: 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: acetic anhydride / 18 h / 0 - 20 °C 1.2: 0.5 h 2.1: ammonium formate / formamide / 18 h / 160 °C 2.2: 0.5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: trichlorophosphate / 1 h / 100 °C 2: hydrogen; sodium acetate / 20% palladium hydroxide-activated charcoal / ethyl acetate; isopropyl alcohol / 2585.81 Torr | ||
Multi-step reaction with 2 steps 1: trichlorophosphate / N,N-dimethyl-formamide / 4 h / 110 °C 2: palladium(II) hydroxide; triethylamine; hydrogen / methanol / 5 h | ||
Multi-step reaction with 2 steps 1: trichlorophosphate; N,N-dimethyl-formamide / 4 h / 110 °C 2: palladium(II) hydroxide; triethylamine; hydrogen / methanol / 5 h |
Multi-step reaction with 2 steps 1: trichlorophosphate / 6 h / 100 °C 2: hydrogen; 20% palladium hydroxide-activated charcoal; triethylamine / ethyl acetate; isopropyl alcohol; water / 20 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: trichlorophosphate / 1 h / 100 °C 2.1: hydrogen; sodium acetate / 20% palladium hydroxide-activated charcoal / ethyl acetate; isopropyl alcohol / 2585.81 Torr 3.1: N-Bromosuccinimide / tetrachloromethane / 1 h / Reflux 3.2: 1 h / Reflux | ||
Multi-step reaction with 6 steps 1.1: trichlorophosphate / N,N-dimethyl-formamide / 4 h / 110 °C 2.1: palladium(II) hydroxide; triethylamine; hydrogen / methanol / 5 h 3.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / benzene / 2 h / 75 °C 4.1: potassium iodide / N,N-dimethyl-formamide / 1 h / 40 °C 4.2: 15 h / 40 °C 5.1: water; sodium hydroxide / tetrahydrofuran / 2 h / 20 °C 6.1: manganese(IV) oxide / dichloromethane / 2 h | ||
Multi-step reaction with 5 steps 1.1: trichlorophosphate; N,N-dimethyl-formamide / 4 h / 110 °C 2.1: palladium(II) hydroxide; triethylamine; hydrogen / methanol / 5 h 3.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / benzene / 2 h / 75 °C 3.2: 1 h / 40 °C 3.3: 15 h / 40 °C 4.1: sodium hydroxide; water / tetrahydrofuran / 2 h / 20 °C 5.1: manganese(IV) oxide / dichloromethane / 2 h |
Multi-step reaction with 4 steps 1: trichlorophosphate / 6 h / 100 °C 2: hydrogen; 20% palladium hydroxide-activated charcoal; triethylamine / ethyl acetate; isopropyl alcohol; water / 20 h / 20 °C 3: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 2.5 h / Reflux 4: pyridine; water / 1.5 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: trichlorophosphate / 2 h / 110 °C 2: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 100 °C 3: potassium iodide / N,N-dimethyl-formamide / 4 h / 35 °C 4: water; sodium hydroxide / tetrahydrofuran / 0.5 h 5: isopropyl alcohol / 12 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: trichlorophosphate / N,N-dimethyl-formamide / 4 h / 110 °C 2.1: palladium(II) hydroxide; triethylamine; hydrogen / methanol / 5 h 3.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / benzene / 2 h / 75 °C 4.1: potassium iodide / N,N-dimethyl-formamide / 1 h / 40 °C 4.2: 15 h / 40 °C | ||
Multi-step reaction with 3 steps 1.1: trichlorophosphate; N,N-dimethyl-formamide / 4 h / 110 °C 2.1: palladium(II) hydroxide; triethylamine; hydrogen / methanol / 5 h 3.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / benzene / 2 h / 75 °C 3.2: 1 h / 40 °C 3.3: 15 h / 40 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: trichlorophosphate / N,N-dimethyl-formamide / 4 h / 110 °C 2.1: palladium(II) hydroxide; triethylamine; hydrogen / methanol / 5 h 3.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / benzene / 2 h / 75 °C 4.1: potassium iodide / N,N-dimethyl-formamide / 1 h / 40 °C 4.2: 15 h / 40 °C 5.1: water; sodium hydroxide / tetrahydrofuran / 2 h / 20 °C | ||
Multi-step reaction with 4 steps 1.1: trichlorophosphate; N,N-dimethyl-formamide / 4 h / 110 °C 2.1: palladium(II) hydroxide; triethylamine; hydrogen / methanol / 5 h 3.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / benzene / 2 h / 75 °C 3.2: 1 h / 40 °C 3.3: 15 h / 40 °C 4.1: sodium hydroxide; water / tetrahydrofuran / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: trichlorophosphate / N,N-dimethyl-formamide / 4 h / 110 °C 2: palladium(II) hydroxide; triethylamine; hydrogen / methanol / 5 h 3: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / benzene / 2 h / 75 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: trichlorophosphate / 6 h / 100 °C 2: hydrogen; 20% palladium hydroxide-activated charcoal; triethylamine / ethyl acetate; isopropyl alcohol; water / 20 h / 20 °C 3: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 2.5 h / Reflux 4: pyridine; water / 1.5 h / 100 °C 5: sodium chlorite; aminosulfonic acid / water; acetone / 2 h / 0 - 40 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: trichlorophosphate / 6 h / 100 °C 2: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 4 h / Reflux; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: trichlorophosphate / 6 h / 100 °C 2: hydrogen; 20% palladium hydroxide-activated charcoal; triethylamine / ethyl acetate; isopropyl alcohol; water / 20 h / 20 °C 3: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 2.5 h / Reflux 4: pyridine; water / 1.5 h / 100 °C 5: sodium chlorite; aminosulfonic acid / water; acetone / 2 h / 0 - 40 °C 6: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / acetonitrile / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: trichlorophosphate / 6 h / 100 °C 2: hydrogen; 20% palladium hydroxide-activated charcoal; triethylamine / ethyl acetate; isopropyl alcohol; water / 20 h / 20 °C 3: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 2.5 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: trichlorophosphate / 6 h / 100 °C 2: hydrogen; 20% palladium hydroxide-activated charcoal; triethylamine / ethyl acetate; isopropyl alcohol; water / 20 h / 20 °C 3: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 2.5 h / Reflux 4: pyridine; water / 1.5 h / 100 °C 5: sodium chlorite; aminosulfonic acid / water; acetone / 2 h / 0 - 40 °C 6: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / acetonitrile / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: trichlorophosphate / 6 h / 100 °C 2: hydrogen; 20% palladium hydroxide-activated charcoal; triethylamine / ethyl acetate; isopropyl alcohol; water / 20 h / 20 °C 3: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 2.5 h / Reflux 4: pyridine; water / 1.5 h / 100 °C 5: sodium chlorite; aminosulfonic acid / water; acetone / 2 h / 0 - 40 °C 6: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / acetonitrile / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: trichlorophosphate / Reflux 2.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 0.5 h / 20 °C 2.2: 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: trichlorophosphate / Reflux 2.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 0.5 h / 20 °C 2.2: 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: trichlorophosphate / Reflux 2.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 0.5 h / 20 °C 2.2: 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: trichlorophosphate / Reflux 2.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 0.5 h / 20 °C 2.2: 80 °C 3.1: zirconium tetrachloride / tetrahydrofuran / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: trichlorophosphate / Reflux 2.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 0.5 h / 20 °C 2.2: 80 °C 3.1: zirconium tetrachloride / tetrahydrofuran / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: trichlorophosphate / Reflux 2.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 0.5 h / 20 °C 2.2: 80 °C 3.1: zirconium tetrachloride / tetrahydrofuran / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: trichlorophosphate / Reflux 2.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 0.5 h / 20 °C 2.2: 80 °C 3.1: zirconium tetrachloride / tetrahydrofuran / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: trichlorophosphate / Reflux 2.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 0.5 h / 20 °C 2.2: 80 °C 3.1: zirconium tetrachloride / tetrahydrofuran / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: trichlorophosphate / Reflux 2.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 0.5 h / 20 °C 2.2: 80 °C 3.1: zirconium tetrachloride / tetrahydrofuran / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: trichlorophosphate / Reflux 2.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 0.5 h / 20 °C 2.2: 80 °C 3.1: zirconium tetrachloride / tetrahydrofuran / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: trichlorophosphate / Reflux 2.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 0.5 h / 20 °C 2.2: 80 °C 3.1: zirconium tetrachloride / tetrahydrofuran / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: trichlorophosphate / Reflux 2.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 0.5 h / 20 °C 2.2: 80 °C 3.1: zirconium tetrachloride / tetrahydrofuran / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: trichlorophosphate / Reflux 2.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 0.5 h / 20 °C 2.2: 80 °C 3.1: zirconium tetrachloride / tetrahydrofuran / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: trichlorophosphate / Reflux 2.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 0.5 h / 20 °C 2.2: 80 °C 3.1: zirconium tetrachloride / tetrahydrofuran / 20 °C |
Tags: 175137-13-0 synthesis path| 175137-13-0 SDS| 175137-13-0 COA| 175137-13-0 purity| 175137-13-0 application| 175137-13-0 NMR| 175137-13-0 COA| 175137-13-0 structure
[ 16228-99-2 ]
4-Methoxythieno[3,2-d]pyrimidine
Similarity: 0.94
[ 16228-99-2 ]
4-Methoxythieno[3,2-d]pyrimidine
Similarity: 0.94
[ 16228-99-2 ]
4-Methoxythieno[3,2-d]pyrimidine
Similarity: 0.94
[ 16228-99-2 ]
4-Methoxythieno[3,2-d]pyrimidine
Similarity: 0.94
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P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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