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CAS No. : | 34408-14-5 | MDL No. : | MFCD01076457 |
Formula : | C10H12ClN5O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MHDPPLULTMGBSI-UUOKFMHZSA-N |
M.W : | 301.69 | Pubchem ID : | 147569 |
Synonyms : |
8-Cl-Ado
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
52% | With N-chloro-succinimide; acetic acid In N,N-dimethyl-formamide at 20℃; for 48 h; | Procedure 2: Adenosine (1.09g, 4.08 mmol) was suspended in DMF (50 mL) and glacial acetic acid (10 mL) was added. A solution of N-chlorosuccinimide (2 g, 15 mmol) in DMF (15 mL) was added dropwise. The reaction mixture was stirred at rt for 48 hours and the volatiles were evaporated in vacuo to give yellow gum. The crude was absorbed on silica and purified by silica gel CC (packed in 5percent MeOHICHC13, eluted with 7percent MeOHICHC13) to yield a white powder (0.65 g, 52 percent).‘H NIVIR (500 MHz, DMSO-d6) 8.16 (s, 1H, H-2), 7.55 (br s, 2H, NH2), 5.86 (d, J = 6.8 Hz, 1H, Hi’), 5.48 (d, J 6.2 Hz, iH, 2’OH), 5.45 (d, J 4.0 Hz, iH, 5’-OH), 5.23 (d, J4.6 Hz, iH, 3’OH), 5.08-5.06 (m, iH, H-2’), 4.23-4.i8 (m, iH, H3’), 4.01-3.96 (m, iH, H4’),3.72-3.65 (m, iH, H5’), 3.57-3.50 (m, iH, H5’). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | With N-chloro-succinimide In N,N-dimethyl-formamide at 45℃; for 18 h; | 6-Benzylamino-9-(β-D-ribofuranosyl)purine (115 mg, 0.322 mmol) and 51.6 mg (0.386 mmol) N-chlorosuccinimide was dissolved in 3 ml DMF and the solution was heated at 45° C. for 18 h. The mixture was evaporated and residue was purified by column chromatography in CHCl3-MeOH-NH4OH (95:5:0.5). Yield 25.2 mg 6-benzylamino-8-chloro-9-(β-D-ribofuranosyl)purine (20percent) a 62.1 mg starting compound (54percent); mp=90-92° C. MS ESI+: 392.2 [M+H+]. For C17H18ClN5O4 calculated 391.1047, found 392.1119 [M+H+]. 1H NMR (300 MHz; CDCl3) δ 3.61 (dd, J=4.1 Hz, 8.2 Hz, H5'), 3.89 (d, J=12.7 Hz, H5'), 4.27 (s, H4'), 4.45 (d, J=5.7 Hz, H3'), 4.74 (bs, -CH2-), 4.79 (bs, -CH2-), 5.00 (dd, J=5.7 Hz, 6.3 Hz, H2'), 6.01 (d, J=7.3 Hz, H1'), 6.38 (bs, H-N), 7.28 (m, H-Ph), 8.21 (s, H2). 8-Chloroadenosine was isolated as an analytical sample for MS ESI by wash out from TLC. MS ESI+: 302.3 [M+H+]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With acetic acid In methanol; N,N-dimethyl-formamide | Method B to a solution of adenosine (1.09 g, 4.1 mmol) in DMF (50 mL) and AcOH (10 mL) was added N-Chlorosuccinamide (NCS, 2.0 g, 15 mmol). The reaction mixture was stirred at room temperature for 6 days. The solvents were evaporated to dryness and the residue was purified by HPLC on a C-18 reverse phase column using MeOH:AcOH:H2 O (18:1:18, v/v) to give 0.8 g (65percent) of 2, which was identical to the title compound prepared by Method A. |