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CAS No. : | 21193-80-6 | MDL No. : | N/A |
Formula : | C11H13BrN4O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZWTPRQXZXQEKFT-IOSLPCCCSA-N |
M.W : | 345.15 | Pubchem ID : | 97186 |
Synonyms : |
|
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: |
* 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 |
---|---|---|
78% | With ammonia; In methanol; at 120 - 130℃; for 16.0h;Sealed tube; | (2R,3R,4R,5R)-4-(benzoyloxy)-2-[(benzoyloxy)methyl]-5-[5-bromo-4-chloro-7H-pyrrole[2,3-d]pyrimidin-7-yl]oxol-3-ylbenzoate (I-4, 7 g, 10.34 mmol) dissolved in ammonia in methanol (60 mL,In saturated with ammonia at 0 C) and placed in a sealed tube. The resulting solution was stirred at 120-130 C for 16 hours and the reaction mixture was concentrated in vacuo.The residue was purified by silica gel column chromatography (eluent: 1-10% methanol in dichloromethane), to give (2R,3R,4S,5R)-2-[4-amino-5-bromo-7H-pyrrolo[2,3-d]pyrimidin-7-yl]-5-(hydroxymethyl)oxolane-3,4-diol (I-5, 2.8 g, yield: 78%) as a white solid |
72% | With ammonia; In methanol; at 100℃; for 4.0h;Sealed tube; | General procedure: The protected nucleoside 2a (473.8 mg, 700 mumol) was suspended in 30 mL 7M ammonia in methanol and heated at 100 C for 4 h in a sealed reaction vessel with stirring. After that, the solution was cooled to ambient temperature and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography sing dichloromethane/methanol (9:1) as eluent, to yield the product as colorless solid (174.0 mg, 504 mumol, 72%). 1H NMR(300 MHz, DMSO-d6) delta 8.10 (1H, s), 7.65 (1H, s), 6.82 (2H, br s), 6.04(1H, d, J=6.2 Hz), 5.35 (1H, d, J=6.5 Hz), 5.25-5.07 (2H, m),4.41-4.29 (1H, m), 4.12-4.02 (1H, m), 3.93-3.83 (1H, m), 3.67-3.47(2H, m); 13C NMR (75 MHz, DMSO-d6) delta 157.0, 152.4, 149.6, 121.8,101.1, 86.8, 86.7, 85.2, 73.9, 70.5, 61.5; HRMS (ESI): m/z calcd forC11H14BrN4O4 [M+H]+ 345.0193, found 345.0198. |
40% | With ammonia; In methanol; at 120℃; for 2.0h; | A solution of (2R,3R,4R,5R)-2-(benzoyloxymethyl)-5-(5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)tetrahydrofuran-3,4-diyl dibenzoate (1) (870 mg, 1.29 mmol) in methanolic ammonia (7 N, 55 mL) was heated at 120 C in a screw-cap pressure flask for 2 h. The mixture was then cooled to rt, and the solvent evaporated under reduced pressure to afford the crude nucleoside. Purification by flash column chromatography (silica gel, 5-15% MeOH/CH2Cl2 gradient) provided (2) as an off-white solid (179 mg, 40%). TLC (silica gel, CH2Cl2/MeOH 6:1): Rf = 0.35. 1H NMR (500 MHz, DMSO-d6) delta: 8.10 (s, 1H, 6-H); 7.66 (s, 1H, 2-H); 6.81 (br s, 2H, 4-NH2); 6.05 (d, J = 6.0 Hz, 1H, 1'-H); 5.32 (d, J = 6.2 Hz, 1H, 2'-OH); 5.15 (d, J = 5.4 Hz, 1H, 3'-OH); 5.11 (d, J = 4.7 Hz, 1H, 5'-OH); 4.35 (m, 1H, 2'-H); 4.07 (m, 1H, 3'-H); 3.89 (m, 1H, 4'-H); 3.62 (m, 1H, 5'-H); 3.54 (m, 1H, 5'-H). LRMS (ESI): 346.2 and 344.4 [M+H]+. |
With ammonium hydroxide; In tetrahydrofuran; at 100℃; for 16.0h;Autoclave; | To a solution of intermediate 21 (6.6 g, 9.75 mmol ) in THF ( 130 niL) was added ammonia (28% in H20, 65 mL ) at room temperature. The reaction mixture was stirred at 100 C (using an autoclave) for 1 6 hours. The reaction mi ture cooled to room temperature and evaporated to dryness under reduced pressure. The residue was taken up into water ( 100 mL) and DCM ( 100 ml. ) and stirred for 1 hour. The layers were separated and the water layer was washed again with DCM ( 100 ml. ) to remove impurities. The water layer was filtered and the filtrate was evaporated to dryness. The residue was purified on flash chromatgraphy on silica (gradient eluention: DCM/MeOH from 95 :5 to 90: 10 ). The desired fractions were collected and the solvent was evaporated, yielding intermediate 22 (3.4 g, crude). The crude product was directly used for the next reaction step w ithout further purification. | |
6.81 g | With methanol; ammonia; In tetrahydrofuran; at 0 - 120℃; for 5.5h;Sealed tube; | i)355i A solution of 56d (20. g, 29 mrnoi) in methanol and THF (2:1, 180 mE) at 0 C in a pressure tube was purged with ammonia gas for 30 minutes. After sealing the tube, the mixture was heated at 120 C for 5 h. The mixture was cooled to RI?, concentrated under reduced pressure, and purified by FCC (Si02. 5-i5% MeOH in DCM) to afford 56e (681 g, 19 mmoi, 67% yield) as a light brown solid, ?H NMR (400 MHz. DMSO-d6): oe 8.09 (s, TH), 7.65 (s, 1H), 7.O0---6.60 (br, 21-1), 6.05 (d, J 6.16 Hz, IFI). 5.33 (d, J::: 6.36 FIz, 1H), 5.16---5.i 1(m, 2Ff), 4.33 (in, 1H), 4.06 (rn, 1H), 3.88 (in, 1H), 3.62 (m, 1H), 3.53 (m, 1H). LCMS purity: 97.6%; LRN?IS (ESI) rn/z caled fbr [M±Hj: 34502/347.02. Found: 345.02/347.02. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | A solution of (2R,3R,4R,5R)-2-(4-Amino-5-bromo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol (2) (160 mg, 0.463 mmol) in hexamethylphosphoramide (2 mL) was cooled to 0 C. Thionyl chloride (0.202 mL, 2.78 mmol) was added dropwise with stirring, and after 10 min, the solution was warmed to rt and stirred a further 18 h. Following dilution with water (5 mL) and adjustment to pH 8 with aqueous NaOH solution (1 M), the aqueous layer was extracted with EtOAc (3 * 5 mL). The combined organic extracts were dried (Na2SO4), filtered, and concentrated under reduced pressure to afford the crude nucleoside. This material was then dissolved in CH2Cl2 and triturated with hexanes to produce a precipitate. The precipitate was collected by filtration, providing pure (3) as an off-white solid (102 mg, 61%). TLC (silica gel, CH2Cl2/MeOH 6:1): Rf = 0.45. LRMS (ESI): 362.1, 364.0 and 365.9 [M+H]+. | |
With N,N,N,N,N,N-hexamethylphosphoric triamide; thionyl chloride; at 0 - 20℃; for 18.1667h;Inert atmosphere; | A solution of 56e (3.51 g, 10 rnmol) in HMPA. (15 mE) under nitrogen atmosphere at 0 C was charged with thionyl chloride (7.3 g, 61 nunol, 4.5 mL) dropwise over 10 miii, then stirred at RI? for 18 h. The reaction mixture was cooled to 0 C, carefully quenched with water (15 mE), and treated with 1 M NaOH until an alkaline pH was obtained. The aqueous mixture was extracted with EtOAc (3x 250 mL). The organic fractions were combined and washed with ice cold water (500 mE), brine (500 mE). dried over Na2SO4, and filtered. The filtrate was concentrated under reduced pressure and purified b FCC (Si02, 5-*i0% MeOH in DCM) to afford 56f (1.0 g, 2.4 mmol. 24% yield) as white sohd. ECMS purity: 88%; LRMS (ESI) ni/z caicd for [MH-H]H: 362.99/364.98. Found: 363.06/365.05. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With ammonia; In methanol; at 20℃; for 8.0h;Inert atmosphere; | NH3/MeOH (3 mL) was added to 2a (30 mg, 0.064 mmol) and the resulting clear solution was stirred at room temperature for 8 h. TLC showed complete conversion of substrate to a more polar product. Volatiles were evaporated and the residue was column chromatographed (10% MeOH in CHCl3) to give 2c (17.5 mg, 80%) as a white powder with NMR data as reported:S2 1H NMR delta 8.10(s, 1H, H2), 7.66 (s, 1H, H8), 7.28, (br s, 2H, NH2), 6.04 (d, 1H, J = 6.2 Hz, H1'), 5.34 (d, 1H, J = 6.4 Hz, 2'-OH), 5.13-5.19 (m, 2H, 3'-OH, 5'-OH) 4.34 (q, 1H, J = 6.1 Hz, H2'), 4.06 ("q", 1H, J= 4.8 Hz, H3'), 3.88 (q, 1H, J = 3.6 Hz, H4'), 3.58-3.64 (m, 1H, H5'), 3.49-3.56 (m, 1H, H5''). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With toluene-4-sulfonic acid; In acetone; at 60℃; for 3.0h; | To a mixture of intermediate 22 ( 1 .0 g, crude) in acetone (32 mL) was added 2,2- dimethoxy propane (1.78 mL g. 14.5 mmol ) and 4-methy lbenzenesu 1 fo n ic acid (0.61 g, 3. 19 mmol) in one portion at room temperature. The mixture was stirred at 60 C for 3 hours. The mixture was cooled to room temperature and quenched by adding saturated aHCO; ( 10 niL) slowly and then extracted with ethyl acetate (50 mL x 5 ). The combined organic phase was washed with saturated brine (120 mL ), dried with MgS04, filtered and concentrated in vacuum, offered intermediate 23 (0.80 g, crude). The crude product was directly used for the next reaction step w ithout further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With trisodium tris(3-sulfophenyl)phosphine; palladium diacetate; sodium carbonate; In water; acetonitrile; at 100℃; for 20.0h;Inert atmosphere; | General procedure: 31 (1 eq.), boronic acid (1.5 eq.) or pinacol ester [for compound14 (1.5 eq.)], Na2CO3 (9 eq.), Pd(OAc)2 (0.05 eq.) and TPPTS (0.15 eq.)were added to a 10mL round-bottom flask, equipped with a stir bar.Next, the flask was evacuated and refilled with argon. This procedure was repeated three times in total. Next, degassed MeCN(2 mL/mmol SM) and H2O (4 mL/mmol SM) were added to the solids under argon. After 5 min of stirring, the mixture was heatedto 100 C in a pre-heated oil bath. When the starting material was fully consumed (usually 1e3 h), the mixture was cooled to ambient temperature, and neutralized (pH ~ 7) with 0.5M aq. HCl. Themixture was evaporated till dryness, resuspended in MeOH and evaporated (three times). Next, the mixture was adsorbed onto Celite (fromMeOH) and eluted over a short silica pad (~5 cm) with 20% MeOH/DCM. The liquid was evaporated in vacuo and purified by column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine; In 1,4-dioxane; water; at 20 - 100℃;Inert atmosphere; | 31 (0.172 g, 0.5 mmol, 1 eq.), 4-pyridinylboronic acid (0.092 g, 0.75 mmol, 1.5 eq.), Pd2(dba)3(0.023 g, 0.025 mmol, 0.05 eq.) and P(c-hexyl)3 (0.017 g, 0.06 mmol,0.12 eq.) were added to a 10mL round-bottom flask, containing astir bar. Next, the flask was evacuated and refilled with argon three times. Then, 1,4-dioxane was added (1.33 mL, 2.67 mL/mmol SM)together with 1.27M aq. K3PO4 solution (0.67 mL, 1.33 mL/mmolSM). The flask was stirred at ambient temperature for ~5 min andthen transferred to a pre-heated oil bath at 100 C. Heating wascontinued for 20 h, after which the mixture was cooled to ambient temperature. The mixture was neutralized (pH ~ 7) with 0.5M aq.HCl. The mixture was evaporated till dryness and re-suspended in MeOH and evaporated (three times). Next, the mixture wasadsorbed onto Celite (from MeOH) and eluted over a short silicapad (~5 cm) with 20% MeOH/DCM. The liquid was evaporated invacuo and purified by column chromatography 5/20% MeOH/EA.15 was isolated as a yellow solid (0.06 g, 0.175 mmol). Yield 35%.Melting point: 260-261 C. 1H NMR (300 MHz, DMSO-d6) delta:3.51-3.58 (m, 1H, H-5??), 3.61-3.68 (m, 1H, H-5'), 3.91 (q, J 3.6 Hz,1H, H-4'), 4.12 (br. s, 1H, H-3'), 4.45 (br. s, 1H, H-2'), 5.13-5.20 (m,2H, OH-3', OH-5'), 5.36 (br. s, 1H, OH-2'), 6.13 (d, J 6.3 Hz, 1H, H-1'), 6.38 (br. s, 2H, NH2), 7.47 (dd, J 4.5, 1.8 Hz, 2H, H-3Pyr, H-5Pyr),7.79 (s, 1H, H-6), 8.18 (s, 1H, H-2), 8.61 (dd, J 4.5, 1.8 Hz, 2H, H-2Pyr,H-6Pyr). 13C NMR (75 MHz, DMSO-d6) delta: 61.6 (C-50), 70.5 (C-30), 73.8(C-20), 85.2 (C-40), 87.1 (C-1?), 99.9 (C-4a), 114.0 (C-5), 122.8 (2C, C-3Pyr, C-5Pyr), 123.0 (C-6), 141.9 (C-4Pyr), 149.9 (2C, C-2Pyr, C-6Pyr),151.5 (C-7a), 152.0 (C-2), 157.4 (C-4). HRMS (ESI): calculated forC16H18N5O4: 344.1353 ([MH]), found: 344.1350. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26% | With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine; In 1,4-dioxane; water; at 20 - 100℃; for 38.0h;Inert atmosphere; | (0.17 g, 0.50 mmol, 1 eq.), pyrimidin-5-yl-boronic acid (0.092 g, 0.75 mmol, 1.5 eq.), Pd2(dba)3 (0.005 g,0.005 mmol, 0.01 eq.) and P(c-hexyl)3 (0.0035 g, 0.012 mmol, 0.024eq.) were added to a 10mL round-bottom flask containing a stir bar.Next, the flask was evacuated and refilled with argon three times.Then, 1,4-dioxane was added (1.33 mL, 2.67 mL/mmol SM) togetherwith 1.27M aq. K3PO4 solution (0.67 mL, 1.3 mL/mmol). The flaskwas stirred at ambient temperature for ~5 min and then transferred to a pre-heated oil bath at 100 C. Heating was continued for 38 h,after which the mixture was cooled to ambient temperature. Themixture was neutralized (pH ~ 7) with 0.5M aq. HCl. The mixturewas evaporated till dryness re-suspended in MeOH and evaporated(three times). Next, the mixture was adsorbed onto Celite (fromMeOH) and eluted over a short silica pad (~5 cm) with 20% MeOH/DCM. The liquid was evaporated in vacuo and purified by columnchromatography 5/20% MeOH/EA. 18 was isolated as a yellowsolid (0.045 g, 0.13 mmol). Yield 26%. Melting point: 275 C(decomposed). 1H NMR (300 MHz, DMSO-d6) delta: 3.50-3.57 (m, 1H,H-5??), 3.60-3.67 (m, 1H, H-5'), 3.91 (q, J 3.6 Hz, 1H, H-4'),4.09-4.14 (m, 1H, H-3'), 4.45 (dd, J 11.1, 5.7 Hz, 1H, H-2'),5.14-5.18 (m, 2H, OH-3' , OH-5'), 5.36 (d, J 6.0 Hz, 1H, OH-2'), 6.13(d, J 6.0 Hz, 1H, H-1'), 6.51 (br. s, 2H, NH2), 7.77 (s, 1H, H-6), 8.18 (s,1H, H-2), 8.86 (s, 2H, H-4Pyrim, H-6Pyrim), 9.13 (s, 1H, H-2Pyrim). 13CNMR (75 MHz, DMSO-d6) delta: 61.6 (C-5'), 70.5 (C-3'), 73.8 (C-2'), 85.2(C-4'), 87.1 (C-1?), 100.3 (C-4a), 109.3 (C-5), 122.8 (C-6), 128.5 (C-5Pyrim), 151.4 (C-7a), 152.0 (C-2), 155.5 (2C, C-4Pyrim, C-6Pyrim), 156.2(C-2Pyrim), 157.6 (C-4). HRMS (ESI): calculated for C15H17N6O4([MH]): 345.1306, found: 345.1329. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With trisodium tris(3-sulfophenyl)phosphine; palladium diacetate; sodium carbonate; In water; acetonitrile; at 100℃;Inert atmosphere; | General procedure: 31 (1 eq.), boronic acid (1.5 eq.) or pinacol ester [for compound14 (1.5 eq.)], Na2CO3 (9 eq.), Pd(OAc)2 (0.05 eq.) and TPPTS (0.15 eq.)were added to a 10mL round-bottom flask, equipped with a stir bar.Next, the flask was evacuated and refilled with argon. This procedure was repeated three times in total. Next, degassed MeCN(2 mL/mmol SM) and H2O (4 mL/mmol SM) were added to the solids under argon. After 5 min of stirring, the mixture was heatedto 100 C in a pre-heated oil bath. When the starting material was fully consumed (usually 1e3 h), the mixture was cooled to ambient temperature, and neutralized (pH ~ 7) with 0.5M aq. HCl. Themixture was evaporated till dryness, resuspended in MeOH and evaporated (three times). Next, the mixture was adsorbed onto Celite (fromMeOH) and eluted over a short silica pad (~5 cm) with 20% MeOH/DCM. The liquid was evaporated in vacuo and purified by column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With trisodium tris(3-sulfophenyl)phosphine; palladium diacetate; sodium carbonate; In water; acetonitrile; at 100℃;Inert atmosphere; | General procedure: 31 (1 eq.), boronic acid (1.5 eq.) or pinacol ester [for compound14 (1.5 eq.)], Na2CO3 (9 eq.), Pd(OAc)2 (0.05 eq.) and TPPTS (0.15 eq.)were added to a 10mL round-bottom flask, equipped with a stir bar.Next, the flask was evacuated and refilled with argon. This procedure was repeated three times in total. Next, degassed MeCN(2 mL/mmol SM) and H2O (4 mL/mmol SM) were added to the solids under argon. After 5 min of stirring, the mixture was heatedto 100 C in a pre-heated oil bath. When the starting material was fully consumed (usually 1e3 h), the mixture was cooled to ambient temperature, and neutralized (pH ~ 7) with 0.5M aq. HCl. Themixture was evaporated till dryness, resuspended in MeOH and evaporated (three times). Next, the mixture was adsorbed onto Celite (fromMeOH) and eluted over a short silica pad (~5 cm) with 20% MeOH/DCM. The liquid was evaporated in vacuo and purified by column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With trisodium tris(3-sulfophenyl)phosphine; palladium diacetate; sodium carbonate; In water; acetonitrile; at 100℃;Inert atmosphere; | General procedure: 31 (1 eq.), boronic acid (1.5 eq.) or pinacol ester [for compound14 (1.5 eq.)], Na2CO3 (9 eq.), Pd(OAc)2 (0.05 eq.) and TPPTS (0.15 eq.)were added to a 10mL round-bottom flask, equipped with a stir bar.Next, the flask was evacuated and refilled with argon. This procedure was repeated three times in total. Next, degassed MeCN(2 mL/mmol SM) and H2O (4 mL/mmol SM) were added to the solids under argon. After 5 min of stirring, the mixture was heatedto 100 C in a pre-heated oil bath. When the starting material was fully consumed (usually 1e3 h), the mixture was cooled to ambient temperature, and neutralized (pH ~ 7) with 0.5M aq. HCl. Themixture was evaporated till dryness, resuspended in MeOH and evaporated (three times). Next, the mixture was adsorbed onto Celite (fromMeOH) and eluted over a short silica pad (~5 cm) with 20% MeOH/DCM. The liquid was evaporated in vacuo and purified by column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
22% | With trisodium tris(3-sulfophenyl)phosphine; palladium diacetate; sodium carbonate; In water; acetonitrile; at 100℃;Inert atmosphere; | General procedure: 31 (1 eq.), boronic acid (1.5 eq.) or pinacol ester [for compound14 (1.5 eq.)], Na2CO3 (9 eq.), Pd(OAc)2 (0.05 eq.) and TPPTS (0.15 eq.)were added to a 10mL round-bottom flask, equipped with a stir bar.Next, the flask was evacuated and refilled with argon. This procedure was repeated three times in total. Next, degassed MeCN(2 mL/mmol SM) and H2O (4 mL/mmol SM) were added to the solids under argon. After 5 min of stirring, the mixture was heatedto 100 C in a pre-heated oil bath. When the starting material was fully consumed (usually 1e3 h), the mixture was cooled to ambient temperature, and neutralized (pH ~ 7) with 0.5M aq. HCl. Themixture was evaporated till dryness, resuspended in MeOH and evaporated (three times). Next, the mixture was adsorbed onto Celite (fromMeOH) and eluted over a short silica pad (~5 cm) with 20% MeOH/DCM. The liquid was evaporated in vacuo and purified by column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With trisodium tris(3-sulfophenyl)phosphine; palladium diacetate; sodium carbonate; In water; acetonitrile; at 100℃;Inert atmosphere; | General procedure: 31 (1 eq.), boronic acid (1.5 eq.) or pinacol ester [for compound14 (1.5 eq.)], Na2CO3 (9 eq.), Pd(OAc)2 (0.05 eq.) and TPPTS (0.15 eq.)were added to a 10mL round-bottom flask, equipped with a stir bar.Next, the flask was evacuated and refilled with argon. This procedure was repeated three times in total. Next, degassed MeCN(2 mL/mmol SM) and H2O (4 mL/mmol SM) were added to the solids under argon. After 5 min of stirring, the mixture was heatedto 100 C in a pre-heated oil bath. When the starting material was fully consumed (usually 1e3 h), the mixture was cooled to ambient temperature, and neutralized (pH ~ 7) with 0.5M aq. HCl. Themixture was evaporated till dryness, resuspended in MeOH and evaporated (three times). Next, the mixture was adsorbed onto Celite (fromMeOH) and eluted over a short silica pad (~5 cm) with 20% MeOH/DCM. The liquid was evaporated in vacuo and purified by column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29% | With trisodium tris(3-sulfophenyl)phosphine; palladium diacetate; sodium carbonate; In water; acetonitrile; at 100℃;Inert atmosphere; | General procedure: 31 (1 eq.), boronic acid (1.5 eq.) or pinacol ester [for compound14 (1.5 eq.)], Na2CO3 (9 eq.), Pd(OAc)2 (0.05 eq.) and TPPTS (0.15 eq.)were added to a 10mL round-bottom flask, equipped with a stir bar.Next, the flask was evacuated and refilled with argon. This procedure was repeated three times in total. Next, degassed MeCN(2 mL/mmol SM) and H2O (4 mL/mmol SM) were added to the solids under argon. After 5 min of stirring, the mixture was heatedto 100 C in a pre-heated oil bath. When the starting material was fully consumed (usually 1e3 h), the mixture was cooled to ambient temperature, and neutralized (pH ~ 7) with 0.5M aq. HCl. Themixture was evaporated till dryness, resuspended in MeOH and evaporated (three times). Next, the mixture was adsorbed onto Celite (fromMeOH) and eluted over a short silica pad (~5 cm) with 20% MeOH/DCM. The liquid was evaporated in vacuo and purified by column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
28% | With trisodium tris(3-sulfophenyl)phosphine; palladium diacetate; sodium carbonate; In water; acetonitrile; at 100℃;Inert atmosphere; | General procedure: 31 (1 eq.), boronic acid (1.5 eq.) or pinacol ester [for compound14 (1.5 eq.)], Na2CO3 (9 eq.), Pd(OAc)2 (0.05 eq.) and TPPTS (0.15 eq.)were added to a 10mL round-bottom flask, equipped with a stir bar.Next, the flask was evacuated and refilled with argon. This procedure was repeated three times in total. Next, degassed MeCN(2 mL/mmol SM) and H2O (4 mL/mmol SM) were added to the solids under argon. After 5 min of stirring, the mixture was heatedto 100 C in a pre-heated oil bath. When the starting material was fully consumed (usually 1e3 h), the mixture was cooled to ambient temperature, and neutralized (pH ~ 7) with 0.5M aq. HCl. Themixture was evaporated till dryness, resuspended in MeOH and evaporated (three times). Next, the mixture was adsorbed onto Celite (fromMeOH) and eluted over a short silica pad (~5 cm) with 20% MeOH/DCM. The liquid was evaporated in vacuo and purified by column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With trisodium tris(3-sulfophenyl)phosphine; palladium diacetate; sodium carbonate; In water; acetonitrile; at 100℃;Inert atmosphere; | General procedure: 31 (1 eq.), boronic acid (1.5 eq.) or pinacol ester [for compound14 (1.5 eq.)], Na2CO3 (9 eq.), Pd(OAc)2 (0.05 eq.) and TPPTS (0.15 eq.)were added to a 10mL round-bottom flask, equipped with a stir bar.Next, the flask was evacuated and refilled with argon. This procedure was repeated three times in total. Next, degassed MeCN(2 mL/mmol SM) and H2O (4 mL/mmol SM) were added to the solids under argon. After 5 min of stirring, the mixture was heatedto 100 C in a pre-heated oil bath. When the starting material was fully consumed (usually 1e3 h), the mixture was cooled to ambient temperature, and neutralized (pH ~ 7) with 0.5M aq. HCl. Themixture was evaporated till dryness, resuspended in MeOH and evaporated (three times). Next, the mixture was adsorbed onto Celite (fromMeOH) and eluted over a short silica pad (~5 cm) with 20% MeOH/DCM. The liquid was evaporated in vacuo and purified by column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | With trisodium tris(3-sulfophenyl)phosphine; palladium diacetate; sodium carbonate; In water; acetonitrile; at 100℃;Inert atmosphere; | General procedure: 31 (1 eq.), boronic acid (1.5 eq.) or pinacol ester [for compound14 (1.5 eq.)], Na2CO3 (9 eq.), Pd(OAc)2 (0.05 eq.) and TPPTS (0.15 eq.)were added to a 10mL round-bottom flask, equipped with a stir bar.Next, the flask was evacuated and refilled with argon. This procedure was repeated three times in total. Next, degassed MeCN(2 mL/mmol SM) and H2O (4 mL/mmol SM) were added to the solids under argon. After 5 min of stirring, the mixture was heatedto 100 C in a pre-heated oil bath. When the starting material was fully consumed (usually 1e3 h), the mixture was cooled to ambient temperature, and neutralized (pH ~ 7) with 0.5M aq. HCl. Themixture was evaporated till dryness, resuspended in MeOH and evaporated (three times). Next, the mixture was adsorbed onto Celite (fromMeOH) and eluted over a short silica pad (~5 cm) with 20% MeOH/DCM. The liquid was evaporated in vacuo and purified by column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With trisodium tris(3-sulfophenyl)phosphine; palladium diacetate; sodium carbonate; In water; acetonitrile; at 100℃;Inert atmosphere; | General procedure: 31 (1 eq.), boronic acid (1.5 eq.) or pinacol ester [for compound14 (1.5 eq.)], Na2CO3 (9 eq.), Pd(OAc)2 (0.05 eq.) and TPPTS (0.15 eq.)were added to a 10mL round-bottom flask, equipped with a stir bar.Next, the flask was evacuated and refilled with argon. This procedure was repeated three times in total. Next, degassed MeCN(2 mL/mmol SM) and H2O (4 mL/mmol SM) were added to the solids under argon. After 5 min of stirring, the mixture was heatedto 100 C in a pre-heated oil bath. When the starting material was fully consumed (usually 1e3 h), the mixture was cooled to ambient temperature, and neutralized (pH ~ 7) with 0.5M aq. HCl. Themixture was evaporated till dryness, resuspended in MeOH and evaporated (three times). Next, the mixture was adsorbed onto Celite (fromMeOH) and eluted over a short silica pad (~5 cm) with 20% MeOH/DCM. The liquid was evaporated in vacuo and purified by column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | General procedure: Compound 3a (86.3 mg, 250 mumol) was dried in a high vacuum prior to phosphorylation and dissolved in 1.5 mL freshly distilled trimethylphosphate by heating. Afterwards, freshly distilled phosphorus oxychloride (76.7 mg, 46.5 muL, 500 mumol) was added and the reaction mixture was stirred in an ice bath for 1 h under argon. Subsequently,the solution was poured into 30 mL 0.08M potassium hydroxide inwater/acetonitrile (2:3) with stirring and neutralized by the addition of1M hydrochloric acid. The volume was reduced and the residue was diluted with 100 mL 0.1M sodium hydrogen carbonate. Then, the solution was dialyzed against water and freeze dried. The obtained solidwas taken up in 25mM triethylammonium acetate buffer and the hydrolyzed acid chloride was isolated by RP-HPLC. The solvent of the collected fractions was removed under reduced pressure and the solid was further desiccated in a high vacuum. After that, the residue was dissolved in a small amount of 0.1M sodium hydrogen carbonate,dialyzed against water and lyophilized, to afford the colorless product as sodium salt (21.4 mg, 50 mumol, 20%). UV-Vis (H2O) lambdamax(epsilon)=278 nm (7750M-1 cm-1); 1H NMR (400 MHz, D2O) delta 8.01 (1H,s), 7.27 (1H, s), 6.20 (1H, s), 4.63-4.46 (3H, m), 4.34-4.25 (2H, m); 13CNMR (75 MHz, D2O) delta 156.7, 152.2, 148.1, 121.4, 101.6, 91.0, 89.1,77.7 (d, J=4.7 Hz), 72.5 (d, J=7.9 Hz), 71.3 (d, J=4.2 Hz), 67.4 (d,J=6.7 Hz); 31P NMR (162 MHz, D2O) delta -1.65; HRMS (ESI): m/z calcdfor C11H11BrN4O6P [M-Na]- 404.9605, found 404.9602. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With 1H-imidazole; In N,N-dimethyl-formamide; at 0℃; | TH1003 (0.345 g, 1 mmol) was dissolved in anhydrous DMF (4 mL, 4 mL / mmol SM) and cooled to 0 C. Then, imidazole (0.17 g, 2.5 mmol, 2.5 eq.) and TBSCI (0.16 g, 1 .05 mmol, 1 .05 eq.) were sequentially added. The resulting solution was stirred at 0 C until TLC showed full conversion of the starting material. Then the mixture was quenched with water, and EA was added. The layers were separated, the water layer extracted twice more with EA. The organic layers were combined, dried over Na2S04, filtered and evaporated till dryness. Purification by column chromatography (2? 8 % MeOH / DCM) gave rise to FH8520 (0.36 g, 0.784 mmol) as a waxy white solid in 78 % yield. 1H NMR (300 MHz, DMSO-d6) delta: 0.09 (s, 3H, CH3), 0.09 (s, 3H, CH3), 0.91 (s, 9H, tBu), 3.73 (dd, J = 1 1 .4, 3.6 Hz, 1 H, H-5"), 3.83 (dd, J = 1 1 .4, 3.6 Hz, 1 H, H-5'), 3.92 (q, J = 3.6 Hz, 1 H, H-4'), 4.07 (dd, J = 9.0, 5.1 Hz, 1 H, H-3'), 4.26 (q, J = 5.4 Hz, 1 H, OH-2'), 5.14 (d, J = 5.1 Hz, 1 H, OH-3'), 5.43 (d, J = 6.0 Hz, 1 H, OH-2'), 6.10 (d, J = 5.4 Hz, 1 H, H-1 '), 6.78 (br. s, 2H, NH2), 7.54 (s, 1 H, H-6), 8.1 1 (s, 1 H, H-2). HRMS (ESI): calculated for C17H28BrN404Si ([M+H]+): 459.1058, found: 459.1058. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | TH1003 (0.125 g, 0.362 mmol) was dissolved in anhydrous pyridine (1 mL, 2.7 mL / mmol) and cooled to - 15C in an isopropanol-dry ice bath. Then, pivaloylchloride (0.136 mL, 1 .1 mmol, 3.04 eq.) was added dropwise. After complete addition, the mixture was kept at - 15 C for 1 hour. Then, the mixture was transferred to an ice-bath (0 C) and stirred for another 2 hours. At that time, mesylchloride (0.084 mL, 1 .08 mmol, 2.97 eq.) was added at 0 C. Next, the ice bath was removed and the mixture stirred at ambient temperature for 3 hours. Then, water was added, together with diethylether. The layers were separated, and the water layer extracted with diethylether twice more. The organic layers were combined, washed with brine and dried over Na2S04, filtered and evaporated till dryness. Next, the mixture was re-dissolved in MeOH (3 mL, 8 mmol / mmol SM) and NaOMe (5.4 M in MeOH) (0.54 mL, 2.9 mmol, 8 eq.) was added, followed by NaBH4 (0.05 g, 1 .28 mmol, 3.54 eq.). The resulting mixture was stirred at ambient temperature overnight. Then acetone (5 mL) was added and stirred for approximately 20 min, after which the mixture was quenched with aq. 0.5 M HCI. The mixture was evaporated till dryness and purified by column chromatography (2? 10 % MeOH / DCM) to yield FH10628 (0.075 g, 0.229 mmol) as a white solid in 63 % yield. 1H NMR (300 MHz, DMSO-d6) delta: 1 .93 (dt, J = 12.6, 8.1 Hz, 1 H, H-3"), 2.23 (dt, J = 12.9, 6.6 Hz, 1 H, H-3'), 3.55 (dt, J = 1 1 .7, 5.4 Hz, 1 H, H-5"), 3.64 (ddd, J = 1 1 .7, 5.4, 3.6 Hz, 1 H, H-5'), 3.99 - 4.06 (m, 1 H, H-4'), 4.40 - 4.48 (m, 1 H, H- 2'), 5.10 (t, J = 5.4 Hz, 1 H, OH-5'), 5.26 (d, J = 5.7 Hz, 1 H, OH-2'), 6.30 (d, J = 5.4 Hz, 1 H, H-1 '), 6.70 (s, 1 H, NH2), 7.58 (s, 1 H, H-6), 8.08 (s, 1 H, H-2). 13C NMR (75 MHz, DMSO-d6) delta: 33.81 (C-3'), 62.63 (C-5'), 70.30 (C-2'), 77.45 (C-4'), 84.00 (C-1 '), 85.35 (C-5), 100.51 (C-4a), 123.27 (C-6), 149.40 (C- 7a), 152.10 (C-2), 156.77 (C-4). HRMS (ESI): calculated for C11H14BrN403 ([M+H]+): 329.0244, found: 329.0249. Melting point: 178 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | TH1003 (0.35 g, 1 mmol) was suspended in anhydrous MeCN (20 mL, 20 mL / mmol SM), and 'moist' MeCN (2 mL, 2 mL / mmol SM; moist = 1 .98 mL MeCN + 0.02 mL water) was added. Next, a-acetoxy- isobutyrylbromide (0.59 mL, 4 mmol, 4 eq.) was added and stirred at ambient temperature for approximately 1 .5H. Next, the reaction was quenched by the addition of aq. sat. NaHC03 / aq. sat. Na2S203 solution and DCM. The water layer was extracted twice more with DCM, organic layers combined, dried over Na2S04, filtered and evaporated. The residue was re-dissolved in 0.4M NaOMe/MeOH (14 mL, 14 mL / mmol SM) and stirred overnight. Next, the mixture was neutralized by the addition of aq. 0.5M HCI, evaporated and purified by column chromatography 1 ? 6 % MeOH/DCM. FH7429_epox (0.25 g, 0.77 mmol) was obtained as a white solid in 77 % yield. 1H NMR (300 MHz, DMSO-d6) delta: 3.46 - 3.59 (m, 2H, H-5', H-5"), 4.12 (t, J = 5.4 Hz, 1 H , H-4'), 4.18 (d, J = 3.0Hz, 1 H, H-3'), 4.30 (d, J = 2.7 Hz, 1 H , H-2'), 5.07 (t, J = 4.8 Hz, 1 H, OH-5'), 6.29 (s, 1 H, H- 1 '), 6.82 (br. s, 2H, NH2), 7.69 (s, 1 H, H-6), 8.14 (s, 1 H, H-2). 13C NMR (75 MHz, DMSO-d6) delta: 57.96 (C-2'), 58.80 (C-3'), 61 .12 (C-5'), 80.77 (C-4'), 81 .71 (C-1 '), 87.06 (C-5), 100.89 (C)-4a), 121 .97 (C-6), 149.40 (C-7a), 152.68 (C-2), 156.97 (C-4). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | With toluene-4-sulfonic acid; orthoformic acid triethyl ester; at 20℃; for 16.0h; | To (2R,3R,4S,5R)-2-[4-amino-5-bromo-7H-pyrrolo[2,3-d]pyrimidin-7-yl]-5-(hydroxymethyl)oxolane-3,4-diol (I-5,3.5g, 10.14mmol)Add triethyl orthoformate (4.55 g, 30.70 mmol) to a solution of acetone (120 mL)And p-toluenesulfonic acid monohydrate (5.5 g, 31.94 mmol), the mixture was stirred at room temperature for 16 hours.The solid was collected by filtration and dried in vacuo to give [(3aR,4R,6R,6aR)-6-[4-amino-5-bromo-7H-pyrrolo[2,3-d]pyrimidin-7-yl]-2,2-dimethyltetrahydro-2H-furo[3,4-d][1,3]dioxolan-4-yl]methanol (I-6,1.25g, yield: 32%) as a white solid |
Tags: 21193-80-6 synthesis path| 21193-80-6 SDS| 21193-80-6 COA| 21193-80-6 purity| 21193-80-6 application| 21193-80-6 NMR| 21193-80-6 COA| 21193-80-6 structure
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