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CAS No. : | 1074-40-4 | MDL No. : | MFCD03428360 |
Formula : | C5H4Cl2N2O | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | WDELVDLDINRUQF-UHFFFAOYSA-N |
M.W : | 179.00 | Pubchem ID : | 12052160 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* 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 |
---|---|---|
With sodium hydrogencarbonate; In ethanol; at 80.0℃; for 3.0h; | Step 1: A solution of <strong>[1074-40-4]4,6-dichloro-2-methoxypyrimidine</strong> (0.7 g), 2,4-dichlorophenethylamine (0.82 g) and sodium bicarbonate (0.88 g) in ethanol (25 mL) is heated at 80° C. for three hours and poured into water (400 mL). The resulting solid is filtered and air dried to afford (6-chloro-2-methoxy-pyrimidin-4-yl)-[2-(2,4-dichloro-phenyl)-ethyl]-amine. | |
With sodium carbonate; In ethanol; at 80.0℃; for 3.0h; | Eurphile I;I- 16-[2-(2.4-DkhIoiO-rhohgHVJ >-ethvS3iJiino|-2-me.hyi-pymidir;-4-yl j-rhoyrrhpsiine-3-alphaifboxyJsc ^cidSic|> . : lambda .sohpiion of 4,6-dich]uro-2-rskappalhoxypyrirHfdine (0,7 g_J, 2-f2,4-dichloro-phelambdayi'}-e.hykitaunipie (0,74 g) and Na>COj (0.88 gs hi EfOH (25 mU is heated at 80"C for 3 hours and poured nio wafer (400 nttj. The resulting solid is filtered and air dried to afford (6<MQro-2-02e.hpsixchi^ggammaj.g^ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate; In ethanol;Heating / reflux; | 83(a)Step 1. A solution of <strong>[1074-40-4]4,6-dichloro-2-methoxypyrimidine</strong> (1 g, 5.59 mmol), 2-aminoindan (0.72 mL, 5.59 mmol) and sodium bicarbonate (0.7 g, 8.38 mmol) in EtOH (25 mL) is refluxed overnight. The reaction is cooled to room temperature, quenched with water (100 mL) and stirred for one hour. The formed precipitate is suction filtered and air dried to afford (6-chloro-2-methoxy-pyrimidin-4-ylV indan-1-yl-amine (1.5 g). LCMS: R? = 3.35 minutes, LCMS: 276, 278 (M+H). | |
With sodium hydrogencarbonate; In ethanol;Heating / reflux; | solution of <strong>[1074-40-4]4,6-dichloro-2-methoxypyrimidine</strong> (1 g, 5.59 mmol), 2-aminoindan (0.72 mL, 5.59 mmol) and sodium bicarbonate (0.7 g, 8.38 mmol) in EtOH (25 mL) is refluxed overnight. The reaction is cooled to room temperature, quenched with water (100 mL) and stirred for one hour. The formed precipitate is suction filtered and air dried to afford (6-chloro-2-methoxy-pyrimidin-4-yl)- indan-1-yl-amine (1.5 g). LCMS: Rtau = 3.35 minutes, LCMS: 276, 278 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate; In ethanol; at 85.0℃; for 5.0h;Heating / reflux; | Step 4. A mixture of <strong>[1074-40-4]4,6-dichloro-2-methoxy-pyrimidine</strong> (0.66 g, 3.69 mmol), 2,2-difluoro-2-phenyl- ethylamine (0.58 g, 3.69 mmol), and NaHCO3 (0.93 g, 11.1 mmol) in 95percent EtOH (10 mL) is heated to reflux. After stirred at 85°C for 5 h. The mixture is diluted with water, filtered, washed (water), and dried to afford (6-chloro-2-methoxy-pyrimidin-4-ylV(2.2-difluoro-2-phenyl-ethyl)-amine as a solid (0.58 g). LCMS: RT = 3.17 minutes, MS: 300 (M+H). 1H NMR (300 MHz, CDCl3) ? 7.57-7.45 (5H, m), 6.1 (IH, s), 5.2 (IH, s), 4.2-4 (2H, m), 3.92 (3H, s). | |
With sodium hydrogencarbonate; In ethanol; at 85.0℃; for 5.0h;Heating / reflux; | A mixture of <strong>[1074-40-4]4,6-dichloro-2-methoxy-pyrimidine</strong> (0,66 g, 3.69 mmol), 2,2-difluoro-2-phenyl- ethylamine (0.58 g, 3.69 mmol), and NaHCO3 (0.93 g, 11.1 mmol) in 95percent EtOH (10 mL) is heated to reflux. After stirred at 850C for 5 h. The mixture is diluted with water, filtered, washed (water), and dried to afford (6-cMoro-2-methoxy-pyrimidm-4-yl)-(2,2-difluoro-2-phenyl-ethyl)-amine as a solid (0.58 g). LCMS: RT = 3.17 minutes, MS: 300 (M+H). 1H NMR (300 MHz, CDCl3) delta 7.57-7.45 (5H, m), 6.1 (IH, s), 5.2 (IH, s), 4.2-4 (2H, m), 3.92 (3H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate; In ethanol; at 80.0℃; for 3.0h; | Step 3. A solution of <strong>[1074-40-4]4,6-dichloro-2-methoxypyrimidine</strong> (0.7 g), 2-(3,4-difluoro-phenyl)-ethylamine (0.66 g) and sodiumbicarbonate (0.88 g) in EtOH (25 mL) is heated at 8O0C for three hours, poured into water (400 mL) and the solid is filtered and air dried to afford (6-chloro-2-methoxy-pyrimidin-4- ylVr2-(3.4-difluoro-phenylVethvll-amine (1.1 g). MS: 312 (M+H); 1H NMR (300 MHz, CDCl3) ? 6.9- 7 (3H, m); 6.05 (lH,s); 3.95 (3H, s); 3.6-3.7 (2H, m); 2.95 (2H, t). | |
With sodium hydrogencarbonate; In ethanol; at 80.0℃; for 3.0h; | A solution of <strong>[1074-40-4]4,6-dichloro-2-methoxypyrimidine</strong> (0.7 g), 2-(3,4-difluoro-phenyl)-ethylamine (0.66 g) and sodiumbicarbonate (0.88 g) in EtOH (25 mL) is heated at 8O0C for three hours, poured into water (400 mL) and the solid is filtered and air dried to afford (6-chloro-2-methoxy-pyrimidin-4- viyr2-f3.4-difluoro-phenvD-ethyl1 -amine (1.1 g). MS: 312 (M+H); 1H NMR (300 MHz, CDCl3) delta 6.9- 7 (3H, m); 6.05 (lH,s); 3.95 (3H, s); 3.6-3.7 (2H, m); 2.95 (2H, t). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate; In ethanol; at 80.0℃; for 3.0h; | Step 3. A solution of <strong>[1074-40-4]4,6-dichloro-2-methoxypyrimidine</strong> [0.7 g, Intermediate (4)], 2-(3-fluoro-4- methoxy-phenyl)-ethylamine [0.66 g, Intermediate (3)] and sodium bicarbonate (0.88 g) in EtOH (25 mL) is heated at 800C for three hours and poured into water (400 mL). The resulting solid is filtered and air dried affording (6-chloro-2-methoxy-pyrimidin-4-ylVr2-(3-fluoro-4-methoxyphenyl)- ethyllamine [1.1 g, Intermediate (5)]. MS: 312 (M+H); 1H NMR (CDCl3): ? 6.9-7 (3H, m); 6.05 (IH, s); 3.95 (3H, s); 3.85 (3H, s); 3.6-3.7 (2H, m); 2.95 (2H, t). | |
With sodium hydrogencarbonate; In ethanol; at 80.0℃; for 3.0h; | A solution of <strong>[1074-40-4]4,6-dichloro-2-methoxypyrimidine</strong> [0.7 g, Intermediate (4)], 2-(3-fluoro-4- methoxy-phenyl)-ethylamine [0.66 g, Intermediate (3)] and sodium bicarbonate (0.88 g) in EtOH (25 mL) is heated at 8O0C for three hours and poured into water (400 mL). The resulting solid is filtered and air dried affording (6-cMoro-2-methoxy-pyrimidin-4-yl)-f2-(3-fluoro-4-methoxyphenyl)- ethyliamine [1.1 g, Intermediate (5)]. MS: 312 (M+H); 1H NMR (CDCl3): delta 6.9-7 (3H, m); 6.05 (IH, s); 3.95 (3H1 s); 3.85 (3H, s); 3.6-3.7 (2H, m); 2.95 (2H, t). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate; In ethanol; at 80.0℃; for 3.0h; | 35(n)Step 1. A solution of <strong>[1074-40-4]4,6-dichloro-2-methoxypyrimidine</strong> [0.7 g, Intermediate (4)], 2-(4-chlorophenyl)- ethylamine (0.66 g) and sodium bicarbonate (0.88g) in EtOH (25 ml) is heated at 80°C for three hours, poured into water (400 mL) and the solid is filtered and air dried affording (6-chloro-2-methoxy- pyrimidin-4-yl)-[2-(4-chlorophenyl)-ethyl]amine [1.1 g, Intermediate (14)]. MS: 299 (M+H). 1H NMR (CDs)2SO]: ? 8 (d, 2H, J=3 Hz); 7.4 (2H, d, J=3 Hz); 6.05 (IH, s); 4 (3H3 s): 3.6-3.7 (2H, m); 2.95 (2H, t). | |
With sodium hydrogencarbonate; In ethanol; at 80.0℃; for 3.0h; | A solution of <strong>[1074-40-4]4,6-dichloro-2-methoxypyrimidine</strong> [0.7 g, Intermediate (4)], 2-(4-chlorophenyl)- ethylamine (0.66 g) and sodium bicarbonate (O.88g) in EtOH (25 ml) is heated at 8O0C for three hours, poured into water (400 mL) and the solid is filtered and air dried affording (6-chloro-2-methoxy- pyrimidin-4-yl)-[2-(4-chlorophenyl)-ethyl]amine [1.1 g, Intermediate (14)]. MS: 299 (M+H). 1H NMR (CD3)2SO]: delta 8 (d, 2H, J=3 Hz); 7.4 (2H1 d, J=3 Hz); 6.05 (IH, s); 4 (3H, s): 3.6-3.7 (2H1 m); 2.95 (2H, t). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With sodium hydrogencarbonate; In ethanol; for 4.0h;Heating / reflux; | Step 3. To a solution of <strong>[1074-40-4]4,6-dichloro-2-methoxy-pyrimidine</strong> (0.606 g, 3.38 mmol, Intermediate (4)] and 2-(2,2-difluoro-benzo[l,3]dioxol-5-yl)-ethylamine hydrochloride (0.884 g, 3.72 mmol, Intermediate (62)]) in EtOH (11 mL) is added sodium bicarbonate (0.85 g, 10.14 mmol) and heated to reflux for 4 hours. The reaction mixture is filtered and filtrate is concentrated, residue solid is washed with small amount of EtOH to yield (6-chloro-2-methoxy-pyrimidin-4-yl)-[2-(2.2-difluoro- benzori.31dioxol-5vn-ethyl]-amine [0.918 g, 79percent, Intermediate (63)] as a solid. LC/MS: MS: 344 (M+H). |
79% | With sodium hydrogencarbonate; In ethanol; for 4.0h;Heating / reflux; | To a solution of <strong>[1074-40-4]4,6-dichloro-2-methoxy-pyrimidine</strong> (0.606 g, 3.38 mmol, Intermediate (4)] and 2-(2,2-difluoro-benzo[l,3]dioxol-5-yl)-ethylamine hydrochloride (0.884 g, 3.72 mmol, Intermediate (62)]) in EtOH (11 mL) is added sodium bicarbonate (0.85 g, 10.14 mmol) and heated to reflux for 4 hours. The reaction mixture is filtered and filtrate is concentrated, residue solid is washed with small amount of EtOH to yield (6-chloro-2-methoxy-pyrimidin-4-yl')-[2-(2,2-difluoro- benzo[l ,31dioxol-5ylVethyll-amine [0.918 g, 79percent, Intermediate (63)] as a solid. LC/MS: MS: 344 (M+H). |
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