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CAS No. : | 582313-57-3 | MDL No. : | MFCD12924542 |
Formula : | C6H3ClFN3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 171.56 | Pubchem ID : | 11321224 |
Synonyms : |
|
TPSA :Topological Polar Surface Area | 41.6 | H-Bond Acceptor Count : | 3 |
XLogP3 : | 1.7 | H-Bond Donor Count : | 1 |
SP3 : | 0.00 | Rotatable Bond Count : | 0 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
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Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 0.5 h; Stage #2: With N-fluorobis(benzenesulfon)imide In tetrahydrofuran at -78℃; for 0.25 h; |
[4-CHLORO-5-BROMO-7H-PYRROLO] [2,3-d] pyrimidine 2 (0.6 g, 2.60 [MMOL)] was dissolved in 30 mL THF (dry), then [COOLED TO-78°C] before adding 4.10 mL nBuLi (1.6 [M] in hexane) dropwise over a period of 10 minutes. The mixture was stirred for 20 minutes [AT-78°C] before adding 3.38 mmol N- fluorobenzene sulfonimide (NFSI) (1.065 g in 6.5 mL dry THF) dropwise over a period of 15 minutes. The mixture was warmed to room temperature overnight, quenched with 2 mL water, and then evaporated to dryness. The crude preparation obtained was partitioned between ethyl acetate (EtOAc) and a saturated solution of ammonium chloride (40 mL/20 mL) then the aqueous layer was extracted with 20 mL of EtOAc and the combined organic layers were washed with 20 mL water. The organic layer was dried with [MGS04,] filtered, and the solvent was evaporated. The crude was purified on silica-gel (silica-gel solid deposit in [MEOH)] with 4percent MeOH/CH2CI2 to provide the title compound (0.36 g, [71 percent YIELD)] ; [1H] NMR (DMSO) : [8] 7.70 (s, 1H) ; 8.62 (s, [1H)] ; 12.25 (s, NH) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With Selectfluor In acetic acid; acetonitrile at 20 - 70℃; for 14 h; | 4-CHLORO-7H-PYRROLOPYRIMIDINE 1 (5 g, 32.7 mmol) and Selectfluor (17.35 g, 49 mmol) were placed in a round bottom flask, followed by the addition of dry acetonitrile (250 mL) and ACOH (50 mL). The solution was then heated at 70 °C for 14 h under N2. After cooling to room temperature, the solvent was removed in vacuo and co-evaporated with toluene (50 mL x 2). The solid was dissolved in a mixture of DCM : EtOAc (1: 1) and filtered through a pad of silica gel which was thoroughly washed. The combined washings were evaporated. And the crude product was then subjected to column chromatography with DCM: EtOAc (4: 1) to give 3.3 g (59percent yield) of 2 as a white SOLID. 1H NMR (DMSO-d6) 8 7.73 (s, 1H), 8.64 (s, 1H), 12.5 (br s, 1H); 13C NMR (DMSO-d6) 8 105.3 (d, J= 14.3 Hz), 111.0 (d, J= 25. 5 Hz), 139.6 (d, J= 244.5 Hz), 146.7 (d, J= 1.5 Hz), 148. 5 (d, J= 3.8 Hz), 151.0 ; 19F NMR (DMSO-D6) 8-170. 7 ( d, J= 1.6 Hz): Mass spectroscopy (MS) measured for C6H3C1FN3 (M+H): 172.0, observed: 172.0. |
58% | With acetic acid; Selectfluor In acetonitrile at 70℃; for 18 h; Inert atmosphere | To a solution of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (2.00 g) in acetonitrile (100 mL) were added acetic acid (20 mL) and N-fluoro-N'-(chloromethyl)triethylenediamine bis(tetrafluoroborate) (6.92 g), and the mixture was stirred under nitrogen atmosphere at 70°C for 18 hours. The reaction mixture was cooled to room temperature, and then concentrated under reduced pressure. To the residue was added methylene chloride/ethyl acetate (1/1), and the solution was passed through a column packed with silica gel (100 mL) and then extracted with methylene chloride/ethyl acetate = 1/1 (2 L). The extract was concentrated, and the resulting residue was purified by column chromatography on silica gel (hexane/ethyl acetate = 70/30 to 35/65) to give 4-chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine (1.30 g) as a powder (yield: 58percent). MS(APCI)m/z; 172/174[M+H]+. |
41% | With acetic acid; Selectfluor In acetonitrile at 70℃; | PREPARATION 144-chloro-5-fluoro-1 /-/-pyrrolo[2,3-c ]pyrimidineA mixture of 6-chloro-7-deazapurine (0.5 g, 3.26 mmol) and Selectfluor.(R). (1.730 g, 4.88 mmol) in CH3CN (25 mL) was treated with AcOH (5 mL) and heated at 70 °C overnight before being cooled and concentrated. Toluene was added and the mixture was concentrated. The residue was dissolved in 1 :1 EtOAc/CH2CI2 and filtered through a pad of silica gel. The filtrate was concentrated and purified via flash column chromatography (20percent EtOAc/CH2CI2) to afford the title compound (0.226 g, 41 percent) as a pink solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.50 (br. s, 1 H), 8.60 - 8.66 (m, 1 H), 7.73 (t, J = 2.51 Hz, 1 H); MS (m/z) 171.9 (M+H+). |
26% | With acetic acid; Selectfluor In acetonitrile at 70℃; for 16 h; | The solution of 4-chloro-7H-pyrrolo[2,3-d]pyrimi- dine Q-1 (10 g, 65.1 mmol) and Selectfluor (27.7 g, 78.1 mmol) in CH3CN (500 mE) and AcOH (100 mE) was stirred at 70° C. for 16 h. (The reaction was done four times, 10 g of Q-1 in each vessel). The reaction solution turned from colorless to black. TEC (CH2C12/CH3OH=20: 1) showed 20percent of the starting material remained, and then the reaction solution was concentrated to give crude solid. The solid was dissolved in EtOAc (1 E), washed with H20 (300 mEx2). The organic layer was concentrated to give Q-2 (7 g) as brown solid. The combined batch four batches were purified by prep-HPEC (0.225percent formic acid/acetonitrile) to give Q-2 (11.6 g, 26percent) as a white solid. ECMS [M+1] 172; ‘H NMR (400 MHz, DMSO-d5) ö ppm 12.47 (s, 1H), 8.62 (s, 1H), 7.72 (d, 1H) |
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