Structure of 755039-54-4
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CAS No. : | 755039-54-4 |
Formula : | C13H17ClN4O |
M.W : | 280.75 |
SMILES Code : | O=C1NC2=CN=C(Cl)N=C2N(C3CCCC3)[C@@H]1CC |
MDL No. : | MFCD11977211 |
Boiling Point : | No data available |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319 |
Precautionary Statements: | P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330 |
* 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 hydride; In ISOPROPYLAMIDE; at -10 - 20℃; for 0.833333h; | 25.0 g of the compound Z3d and 6.5 mL (0.1 mol) methyl iodide were placed in 250 mL dimethylacetamide and at -10 C. 3.8 g (0.95 mol) sodium hydride were added as a 60% dispersion in mineral oil. The mixture was stirred for 20 min. at 0 C., then 30 min. at ambient temperature and finally ice was added. The reaction mixture was evaporated down and combined with 300 mL water. The precipitate formed was suction filtered and washed with petroleum ether. Yield: 23.0 g of a compound Z3e (colourless solid) | |
With sodium hydride; In ISOPROPYLAMIDE; at -10 - 20℃; for 0.833333h; | 25.0 g of the compound Z3d and 6.5 mL (0.1 mol) methyl iodide are placed in 250 mL dimethylacetamide and at -100C 3.8 g (0.95 mol) sodium hydride as a 60% dispersion in mineral oil is added. It is stirred for 20 min at 00C, then for 30 min at ambient temperature and finally ice is added. The reaction mixture is evaporated down and combined with 300 mL water. The precipitate formed is suction filtered and washed with petroleum ether. Yield: 23.0 g of a compound Z3e (colourless solid) | |
With sodium hydride; In ISOPROPYLAMIDE; at 0 - 20℃; for 0.833333h; | 25.0 g of the compound Z3d and 6.5 mL (0.1 mol) methyl iodide are placed in 250 mL dimethylacetamide and at -10 C. 3.8 g (0.95 mol) sodium hydride are added as a 60% dispersion in mineral oil. The mixture is stirred for 20 min. at 0 C., then 30 min. at ambient temperature and finally ice is added. The reaction mixture is evaporated down and combined with 300 mL water. The precipitate formed is suction filtered and washed with petroleum ether. Yield: 23.0 g of a compound Z3e (colourless solid) |
With sodium hydride; In ISOPROPYLAMIDE; at 4 - 20℃; for 7.0h; | Preparation of Compound 9; 38 g (0.95 mol) sodium hydride (60% dispersion in mineral oil) are added batchwise to a solution of 264 g (0.94 mol) of 8 and 161 g (1.13 mol) methyl iodide in 2 L dimethylacetamide at 4-10 C. within one hour. The cooling bath is removed and the mixture is allowed to come up to 20 C. within 2 hours. It is cooled to 10 C. and a further 0.38 g (9.5 mmol) sodium hydride are added. The mixture is stirred for 4 hours at 10-15 C. 100 mL ethyl acetate and 1 kg ice are added to the reaction solution. The resulting suspension is diluted with 3 L demineralised water. The suspension is stirred for 2 hours, the precipitate is suction filtered and the filter cake is washed with demineralised water. The product is dried at 50 C. in the vacuum drying cupboard. 273 g of product 9 are obtained as colourless crystals. | |
With sodium hydride; In N,N-dimethyl acetamide; mineral oil; at 0 - 20℃; for 0.833333h; | 25.0 g of the compound Z3d and 6.5 mL (0.1 mol) methyl iodide were placed in 250 mL dimethylacetamide and at -10 C. 3.8 g (0.95 mol) sodium hydride as a 60% dispersion in mineral oil was added. It was stirred for 20 min at 0 C., then for 30 min at ambient temperature and finally ice was added. The reaction mixture was evaporated down and combined with 300 mL water. The precipitate formed was suction filtered and washed with petroleum ether. Yield: 23.0 g of a compound Z3e (colourless solid) | |
With sodium hydride; In ISOPROPYLAMIDE; at 4 - 20℃; for 7.0h;Product distribution / selectivity; | 38 g (0.95 mol) sodium hydride (60% dispersion in mineral oil) are added batchwise to a solution of 264 g (0.94 mol) of 8 and 161 g (1.13 mol) methyl iodide in 2 L dimethylacetamide at 4-10 C. within one hour. The cooling bath is removed and the mixture is allowed to come up to 20 C. within 2 hours. It is cooled to 10 C. and a further 0.38 g (9.5 mmol) sodium hydride are added. The mixture is stirred for 4 hours at 10-15 C. 100 mL ethyl acetate and 1 kg ice are added to the reaction solution. The resulting suspension is diluted with 3 L demineralised water. The suspension is stirred for 2 hours, the precipitate is suction filtered and the filter cake is washed with demineralised water. The product is dried at 50 C. in the vacuum drying cupboard. 273 g of product 9 are obtained as colourless crystals. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In dimethylcarbonate; at 130℃; for 6.0h;Autoclave;Product distribution / selectivity; | A suspension of 100 g (356 mmol) 8 and 73.8 g (534 mmol) potassium carbonate in 400 mL dimethylcarbonate is heated to 130 C. in an autoclave for 6 hours. The mixture is left to cool and 300 mL demineralised water and 200 mL ethyl acetate are added with stirring. The aqueous phase is separated off together with undissolved salts. 500 mL of solvent are distilled off from the organic phase at a pressure 180 mbar and a heating bath temperature of 70 C. 600 mL demineralised water are added to the residue and 100 mL solvent are distilled off at a pressure of 150 mbar and a heating bath temperature of 80 C. 350 mL ethanol are added to the suspension which is then heated to 65 C. The solution is left to cool and inoculated. It is cooled to 10 C., the precipitate is suction filtered and washed with a mixture of demineralised water and ethanol (2.5:1). The product is dried at 50 C. in the vacuum drying cupboard. 95.5 g product 2 are obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With potassium carbonate; In 1,4-dioxane; at 90℃; for 6.0h;Inert atmosphere; | Compound IV (260 mg, 0.93 mmol) was dissolved in dioxane (5 ml).Trimethylphosphate (650 mg, 4.6 mmol) and K2CO3 (192 mg, 1.39 mmol) were added, and the reaction mixture was stirred under 2 at 90 C for 6hr until the starting material was consumed. The reaction mixture was diluted with water and extracted with EtOAc. The solvent was removed, and the residue was purified by silica gel column chromatography (PE: EtOAc=l : l) to give intermediate B as a white solid (270 mg, 86 %). ¾ NMR (CDCI3) delta: 7.7 (s, 1H), 4.34 (m, 1H), 4.25 (m, 1H), 3.33 (s, 3H), 2.1-1.6 (m, 10H) and 0.86 ppm (t, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With potassium carbonate; In acetone; for 2.0h;Reflux; Inert atmosphere; | Step 11 (7R)-2-chloro-8-cyclopentyl-7-ethyl-5-methyl-5H-pteridin-6-one; (7R)-2-Chloro-8-cyclopentyl-7-ethyl-7,8-dihydro-5H-pteridin-6-one In (3.50 g, 12.50 mmol) was dissolved in 80 mL of acetone followed by the addition of methyl p-toluenesulfonate (3.40 g, 18.70 mmol) and potassium carbonate (3.45 g, 25 mmol). The resulting mixture was heated to reflux for 2 hours with stirring and then cooled down to room temperature. The reaction mxiture was filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound (7R)-2-chloro-8-cyclopentyl-7-ethyl-5-methyl-5H-pteridin-6-one 1o (3.40 g, yield: 93.0%) as a white solid. MS m/z (ESI): 295.4 [M+1] |
93% | With potassium carbonate; In acetone; for 2.0h;Reflux; | Step 11 (7R)-2-chloro-8-cyclopentyl-7-ethyl-5-methyl-5H-pteridin-6-one (7R)-2-Chloro-8-cyclopentyl-7-ethyl-7,8-dihydro-5H-pteridin-6-one 1n (3.50 g, 12.50 mmol) was dissolved in 80 mL of acetone followed by the addition of methyl p-toluenesulfonate (3.40 g, 18.70 mmol) and potassium carbonate (3.45 g, 25 mmol). The resulting mixture was heated to reflux for 2 hours with stirring and then cooled down to room temperature. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound (7R)-2-chloro-8-cyclopentyl-7-ethyl-5-methyl-5H-pteridin-6-one 1o (3.40 g, yield: 93.0%) as a white solid.MS m/z (ESI): 295.4 [M+1] |
Tags: 755039-54-4 synthesis path| 755039-54-4 SDS| 755039-54-4 COA| 755039-54-4 purity| 755039-54-4 application| 755039-54-4 NMR| 755039-54-4 COA| 755039-54-4 structure
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