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CAS No. : | 114248-23-6 | MDL No. : | MFCD00871912 |
Formula : | C9H10F2N2O5 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FIRDBEQIJQERSE-QPPQHZFASA-N |
M.W : | 264.18 | Pubchem ID : | 9871558 |
Synonyms : |
dFdU;2',2'-Difluoro-2'-deoxyuridine
|
Chemical Name : | 1-((2R,4R,5R)-3,3-Difluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
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 |
---|---|---|
77.7% | With pyridine; at 0 - 25℃; | To a solution of 298-1 (12 g, 45.42 mmol) in pyridine (100 mL) was added DMTrCl (16.16 g, 47.69 mmol) in portions at 0 C. over a period of 30 mins under N2. The mixture was warmed to 25 C. and stirred for 16 h. LCMS and TLC (DCM:MeOH=20:1) showed that the starting material was consumed. The reaction was quenched with MeOH (10 mL) and then concentrated in vacuum. The residue was purified by silica gel chromatography (100-200 mesh silica gel, PE:EA2981:1) to give pure DMTr-298-1 (20 g, 77.7%) as a white solid |
With pyridine; at 0 - 20℃; for 15h; | 102991 To a solution of P24-4 (21.0 g, 79.5 mmol) in pyridine (250 mL) was added DMTrC1 (28.2 g, 83.5 mmol) at 0C. The solution was stirred at R.T. for 15 hours. The reaction was quenched with MeOH and concentrated to dryness under reduced pressure. The residue was dissolved in EtOAc and washed with water. The organic layer was dried over Na2SO4 and concentrated. The residue was dissolved in DCM (300 mL). Imidazole (13.6 g, 200 mmol) and TBSC1 (30.0 g, 200 mmol) were added. The reaction mixture was stirred at R.T. for 12 hours. The reaction mixture was washed with NaHCO3 and brine. The organic layer was dried over Na2SO4 and concentrated. The residue (48.5 g, 79.5 mniol) was dissolved in 80% HOAc aq. solution (400 mL). The mixture was stirred at R.T. for 20 hours. The mixture was diluted with EtOAc and washed with NaHCO3 solution and brine. The organic layer was dried over Na2SO4 and purified by silica gel column chromatography (1- 2% MeOH in DCM) to give P24-5 as a white solid (21.0 g, 70%). ESI-MS: m/z 379.1 [M+H1. | |
With pyridine; at 20℃; for 15h; | To a solution of 1-1 (100.0 g, 378.7 mmol) in pyriHOdine (750 mL) was added DMTrC1 (164.9 g, 487.8 mmol). added, and the mixture was concentrated to dryness under The solution was stirred at RT for 15 h. MeOH (300 mL) wasreduced pressure. The residue was dissolved in EA andwashed with water. The organic layer was dried over Na2504and concentrated. The residue was dissolved in DCM (500mL). To this solution were added imidazole (44.3 g, 650.4 mmol) and TI3SC1 (91.9 g, 609.8 mmol). The mixture was stirred at RT for 14 h. The solution was washed with NaHCO3 and brine. The organic layer was dried over Na2SO4, and concentrated to give the crude product as a light yellow solid. The crude (236.4 g, 347.6 mmol) was dissolved in 80% HOAc aqueous solution (500 mE). The mixture was stirred at RT for 15 h. The mixture was diluted with EA, and washed with NaHCO3 solution and brine. The organic layer was dried over Na2SO4 and purified on a silica gel colunm chromatography (1-2% MeOH in DCM) to give 1-2 (131.2 g, 91.9%) as a light yellow solid. ESI-MS: mlz 802 [M+H]. |
With pyridine; at 20℃; for 15h; | To a solution of 1-1 (100.0 g, 378.7 mmol) in pyridine (750 mL) was added DMTrCl (164.9 g, 487.8 mmol). The solution was stirred at RT for 15 h. MeOH (300 mL) was added, and the mixture was concentrated to dryness under reduced pressure. The residue was dissolved in EA and washed with water. The organic layer was dried over Na2SO4 and concentrated. The residue was dissolved in DCM (500 mL). To this solution were added imidazole (44.3 g, 650.4 mmol) and TBSCl (91.9 g, 609.8 mmol). The mixture was stirred at RT for 14 h. The solution was washed with NaHCO3 and brine. The organic layer was dried over Na2SO4, and concentrated to give the crude product as a light yellow solid. The crude (236.4 g, 347.6 mmol) was dissolved in 80% HOAc aqueous solution (500 mL). The mixture was stirred at RT for 15 h. The mixture was diluted with EA, and washed with NaHCO3 solution and brine. The organic layer was dried over Na2SO4 and purified on a silica gel column chromatography (1-2% MeOH in DCM) to give 1-2 (131.2 g, 91.9%) as a light yellow solid. ESI-MS: m/z 802 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With acetic acid; sodium nitrite; In water; at 20℃; for 48h; | formula 11(5 g, 16.7 mmol, 1.0 eq.) Was dissolved in a 2N aqueous acetic acid solution (350 ml) Sodium nitrite (16.7 g, 14.5 eq.) Was added slowly and left at room temperature for 48 hours. 2N The mixture was adjusted to pH 6-7 with aqueous sodium hydroxide solution and then concentrated under reduced pressure. Decompression concentration After the addition of methanol / ethyl acetate (1: 5, 360 ml), the insoluble salts were removed. This process The salt was removed repeatedly several times to concentrate under reduced pressure to obtain 4.22 g of a light brown transparent oil of formula (7) in 95% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With ammonia; In methanol; at 20℃; for 12h; | Compound 68-3 was dissolved in NH3/MeOH (600 mL) and stirred overnight. The solvent was concentratedto give the residue, which was purified by silica gel column chromatography (5% MeOH in DCM) to give68-4 (12 g, 99%) as a white solid |
99% | With ammonia; In methanol; | Compound 68-3 was dissolved in NH3/MeOH (600 mL) and stirred overnight. The solvent was concentrated to give the residue, which was purified by silica gel column chromatography (5% MeOH in DCM) to give 68-4 (12 g, 99%) as a white solid. |
95.8% | With ammonia; In methanol; at 20℃; for 15h; | P24-3 (39.2 g, 83 mmol) was dissolved in saturated methanolic ammonia, and the resulting solution was stirred at R.T. for 15 hours. The solvent was removed, and the residue was purified on a silica gel column (DCM/MeOH=50:1 to 20:1) to give P24-4 (21.0 g, 95.8%). |
95.8% | With ammonia; In methanol; at 20℃; for 15h; | j0298j Compound P24-3 (39.2 g, 83 mmol) was dissolved in saturated methanolic ammonia, and the resulting solution was stirred at R.T. for 15 hours. The solvent was removed, and the residue was purified on a silica gel column (DCM/MeOH = 50:1 to 20:1) to give P24-4 (21.0 g, 95.8%). |
12 g | With ammonia; In methanol; | Compound 68-3 was dissolved in NH3/MeOH (600mL) and stirred overnight. The solvent was concentrated togive the residue, which was purified by silica gel columnchromatography (5% MeOH in DCM) to give 68-4 (12 g,99%) as a white solid. |