* 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.
With ammonium formate In methanol at 75℃; for 4 h;
2-Amino-3H-pyrrolo[3,2-0C for 4 h. After completion of the reaction, the reaction mixture was cooled and filtered through a pad of Celite with hot 1 : 1 DMF/MeOΗ. The filtrate was concentrated in vacuo to provide the product as an off-white solid (6.2 g, 99percent).
With sodium dithionite In water for 2 h; Heating / reflux
A mixture of 10 (24 g) and sodium dithionite (48 g) in water (240 ml) was heated under reflux for 2 h.. The suspension was hot filtered, cooled and then filtered to give 2 (7.84 g, 61percent) as a yellow/brown solid.. Recrystallized from water it had mp>300° C. 1H NMR (d6-DMSO) was as reported.3 13C NMR δ 155.9, 152.0, 146.6, 128.3, 113.6, 101.2.
Reference：
[1] Journal of Organic Chemistry, 1999, vol. 64, # 22, p. 8411 - 8412
[2] Patent: US6693193, 2004, B1, . Location in patent: Page column 11-12; 16
Stage #1: With triethylamine; mercury dichloride In N,N-dimethyl-formamide at 26℃; Stage #2: With sodium acetate In methanol at 0 - 20℃; Stage #3: With sodium hydroxide In methanol; water at 60℃; for 0.5 h;
Preparation of Intermediate DDTo a mixture of Intermediate CC (200 mg, 1.049 mmol), Et3N (0.436 mL, 3.14 mmol), and l ,3-dicarbomethoxy-2-methyl-2-thiopseudourea (216 mg, 1.049 mmol) in DMF (8 mL) was added HgCl2 (284 mg, 1.049 mmol) at room temperature (26 °C). The mixture was stirred overnight. The reaction mixture was then filtered, and the filtrate was diluted with H20 (50 mL), extracted with EtOAc (-150 mL), washed with H20 (50 mL) and brine solution (50 mL), dried (Na2SC>4), filtered, and evaporated to obtain crude Intermediate DD (150 mg). This material was used in the next step without any further characterization and purification. Rf = 0.3 (20percentEtO Ac/petroleum ether). Mass: (m z=313.1).Preparation of Compound (33)To a solution of Intermediate DD (150 mg, 0.48 mmol) in MeOH ( 10 mL) was added NaOMe (129 mg, 2.40 mmol) at 0 °C. The reaction was warmed to room temperature and stirred overnight. The reaction mixture was concentrated, and IN aqueous NaOH (2.5 mL) was added. The reaction was heated to 60 °C for 30 minutes. The reaction mixture was evaporated to obtain a crude residue that was purified by column chromatography (100-200 mesh silica gel, 20percent) MeOH/CHCl3/aq. NH3) to obtain Compound (33) (15 mg, 9.6percent). Rf = 0.6 (20percent MeOH/CHCl3/0.1 mL aqueous NH3). 1H-NMR (400MHz, DMSO-J6) δ 11.36 and 1 1.20 (2 overlapped br. s, exchanged with D20, 2H), 7.05 (s, 1H), 6.05 (br. s, exchanged with D20, 2H), 5.88 (d, J = 2.4Hz, 1H). Mass (m/z): 150.7 (M++l). LCMS: (Column: Zodiacsil 120-5-C- 18-Aq (4.6 χ 50 mm), Mobile phase: A: 0.01M HCOONH4 (Aq); B: MeOH, T/percentB: 0/5, 10/90, 10.1/5, Flow: 1.0 mL/min, Diluent: MeOH), Rt=2.379 min, 97.08 (214 nm), 98.26 (254 nm).
With sodium hydroxide In water for 0.25 h; Microwave irradiation
In the sequence, in a microwave tube was added 4 (200 mg,0.97 mmol) and NaOH (195.0 mg, 4.84 mmol) in H2O (5 mL). Theset conditions were 95 C for 15 min with an average power of40 W. This procedure was repeated four times and then the crudeproducts were mixed. The solvent was evaporated under vacuumand then water (5 mL) was added. The mixture was acidified topH 5.0 with glacial acetic acid. The precipitate was filtered andthen recrystallized in ethanol/H2O (3:1) affording the desired product5 in 96percent yield (701.0 mg)
Reference：
[1] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 2, p. 226 - 231
6
[ 151587-58-5 ]
[ 65996-58-9 ]
Reference：
[1] Tetrahedron Letters, 1993, vol. 34, # 29, p. 4595 - 4598
[2] Journal of Organic Chemistry, 1995, vol. 60, # 24, p. 7947 - 7952
[3] Patent: US6693193, 2004, B1, . Location in patent: Page column 10-11
7
[ 4214-85-1 ]
[ 65996-58-9 ]
Reference：
[1] Journal of Organic Chemistry, 1999, vol. 64, # 22, p. 8411 - 8412
[2] Journal of Organic Chemistry, 1995, vol. 60, # 24, p. 7947 - 7952
[3] Tetrahedron Letters, 1993, vol. 34, # 29, p. 4595 - 4598
[4] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 2, p. 226 - 231
[5] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 2, p. 226 - 231
[6] Patent: WO2006/122003, 2006, A2,
8
[ 151587-54-1 ]
[ 65996-58-9 ]
Reference：
[1] Synthetic Communications, 2002, vol. 32, # 24, p. 3797 - 3802
[2] Journal of Organic Chemistry, 1995, vol. 60, # 24, p. 7947 - 7952
[3] Tetrahedron Letters, 1993, vol. 34, # 29, p. 4595 - 4598
9
[ 3977-29-5 ]
[ 65996-58-9 ]
Reference：
[1] Journal of Organic Chemistry, 1995, vol. 60, # 24, p. 7947 - 7952
[2] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 2, p. 226 - 231
[3] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 2, p. 226 - 231
[4] Patent: WO2006/122003, 2006, A2,
With sodium dithionite; In water; for 2h;Heating / reflux;
A mixture of 10 (24 g) and sodium dithionite (48 g) in water (240 ml) was heated under reflux for 2 h.. The suspension was hot filtered, cooled and then filtered to give 2 (7.84 g, 61%) as a yellow/brown solid.. Recrystallized from water it had mp>300 C. 1H NMR (d6-DMSO) was as reported.3 13C NMR delta 155.9, 152.0, 146.6, 128.3, 113.6, 101.2.
2-amino-1,5-dihydro-7-(phenylcarbonyl)-4H-pyrrolo[3,2-d]pyrimidin-4-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
53%
Amixture of 9-deazapurine 5 (150.0 mg, 1.0 mmol) and benzoylchloride (2.2 equiv) in trifluoromethanesulfonic acid (3.45 g,23 mmol) was stirred at 80-120 C for 48 h. After the mixturewas cooled and H2O (15 mL) was added. Then the reaction wasneutralized with NaOH 1.0 mol/L, the volume adjusted to approximately35 mL by adding H2O and then 60 equiv of NaOH wereadded. The reaction was stirred for 2.5 h at 60 C. The mixturewas neutralized with glacial acetic acid and the formed solid wasfiltered under vacuum and washed several times with dichloromethane(10 mL), ethyl acetate (10 mL), acetone (5 mL) andmethanol (5 mL). The precipitate purity was monitored by CCDand depending on the product, further purification was necessaryby recrystallization in methanol or flash chromatography usingCH2Cl2/MeOH (4:1) as eluent.
2-amino-3H,5H-7-(3',4'-dichlorobenzoyl)pyrrolo[3,2-d]pyrimidin-4-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
75%
General procedure: Amixture of 9-deazapurine 5 (150.0 mg, 1.0 mmol) and benzoylchloride (2.2 equiv) in trifluoromethanesulfonic acid (3.45 g,23 mmol) was stirred at 80-120 C for 48 h. After the mixturewas cooled and H2O (15 mL) was added. Then the reaction wasneutralized with NaOH 1.0 mol/L, the volume adjusted to approximately35 mL by adding H2O and then 60 equiv of NaOH wereadded. The reaction was stirred for 2.5 h at 60 C. The mixturewas neutralized with glacial acetic acid and the formed solid wasfiltered under vacuum and washed several times with dichloromethane(10 mL), ethyl acetate (10 mL), acetone (5 mL) andmethanol (5 mL). The precipitate purity was monitored by CCDand depending on the product, further purification was necessaryby recrystallization in methanol or flash chromatography usingCH2Cl2/MeOH (4:1) as eluent.
2-amino-3H,5H-7-(3',5'-dichlorobenzoyl)pyrrolo[3,2-d]pyrimidin-4-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
62%
General procedure: Amixture of 9-deazapurine 5 (150.0 mg, 1.0 mmol) and benzoylchloride (2.2 equiv) in trifluoromethanesulfonic acid (3.45 g,23 mmol) was stirred at 80-120 C for 48 h. After the mixturewas cooled and H2O (15 mL) was added. Then the reaction wasneutralized with NaOH 1.0 mol/L, the volume adjusted to approximately35 mL by adding H2O and then 60 equiv of NaOH wereadded. The reaction was stirred for 2.5 h at 60 C. The mixturewas neutralized with glacial acetic acid and the formed solid wasfiltered under vacuum and washed several times with dichloromethane(10 mL), ethyl acetate (10 mL), acetone (5 mL) andmethanol (5 mL). The precipitate purity was monitored by CCDand depending on the product, further purification was necessaryby recrystallization in methanol or flash chromatography usingCH2Cl2/MeOH (4:1) as eluent.
2-amino-3H,5H-7-(m-nitrobenzoyl)pyrrolo[3,2-d]pyrimidin-4-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
68%
General procedure: Amixture of 9-deazapurine 5 (150.0 mg, 1.0 mmol) and benzoylchloride (2.2 equiv) in trifluoromethanesulfonic acid (3.45 g,23 mmol) was stirred at 80-120 C for 48 h. After the mixturewas cooled and H2O (15 mL) was added. Then the reaction wasneutralized with NaOH 1.0 mol/L, the volume adjusted to approximately35 mL by adding H2O and then 60 equiv of NaOH wereadded. The reaction was stirred for 2.5 h at 60 C. The mixturewas neutralized with glacial acetic acid and the formed solid wasfiltered under vacuum and washed several times with dichloromethane(10 mL), ethyl acetate (10 mL), acetone (5 mL) andmethanol (5 mL). The precipitate purity was monitored by CCDand depending on the product, further purification was necessaryby recrystallization in methanol or flash chromatography usingCH2Cl2/MeOH (4:1) as eluent.
2-O-methyl-1,3,5-tri-O-benzoyl-β-D-ribofuranose[ No CAS ]
[ 65996-58-9 ]
2-amino-7-(2-O-methyl-β-D-ribofuranosyl)-5H-pyrrolo[3,2-d]pyrimidin-4(3H)-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
To a suspension of 2-amino-SH-pyrrolo [3, [2-D] PYRIMIDIN-4 (3H)-ONE] (9- deazaguanine) (0.454 g, 3.0 mmol) (prepared according to J. Org. Chem. 1978,43, 2536) and 2-O-methyl-1, 3, [5-TRI-O-BENZOYL-D-D-RIBOFURANOSE] (1.54 g, 3.2 mmol) in dry nitromethane (23 mL) at [60C] was added stannic chloride (0.54 mL, 4.5 mmol). The reaction mixture was maintained at this temperature for 0.5 hr. , cooled and poured onto ice-cold saturated sodium bicarbonate solution (70 mL). The insoluble material was filtered through florisil and washed with ethyl acetate [(3X50] mL). The filtrate was extracted with ethyl acetate [(2X50] mL), and organic layer was washed with water [(2X50] mL), dried over [NA2SO4] and evaporated to dryness. Chromatography of the resulting foam on silica gel with [CH2CI2/MEOH] (14: 1) afforded the benzoylated product (0.419 g, 30% yield). To a suspension of the benzoylated product (0.25 g) in MeOH (2.4 mL) was added t-butylamine (0.52 [ML)] and stirring at room temperature was continued for 24 hrs. followed by addition of more t-butylamine [(0. 2] mL). The reaction mixture was stirred at ambient temperature overnight, concentrated in vacuum and the residue was purified by flash chromatography over silica gel using CH2Cl2/MeOH (85: 15) as eluent giving the desired compound as a foam (0.80 g). 'H NMR [(200MHZ,] [DMSO-D6)] : [3] Hz3.28 (s, 3H), 3.40-3. 52 (m, 3H), 3.87-3. 90 (m, 1H), 4.08-4. 09 (m, 1H), 4.67 (d, 1H, J = 5.2 Hz), 4.74 (d, 1H, J = 7.0 Hz), 5.62 and 5.50 (2 bs, 3H), 7.14 (d, 1H, [J=] 2.6 Hz), 10.43 (s, [LH),] 11.38 (s, [LH)] ; Mass spectrum: calcd. for C12H16N4O5: 296. 28; found: 295.11.
(3R,4R)-3-hydroxy-4-(hydroxymethyl)pyrrolidine hydrochloride[ No CAS ]
[ 615580-48-8 ]
Yield
Reaction Conditions
Operation in experiment
In water; at 95℃; for 12h;
(3R, 4R)-3-Hydroxy-4- [(HYDROXYMETHYL) PYRROLIDINE HYDROCHLORIDE] (4) (154 mg, 1.0 [MMOL)] and sodium acetate (82 mg, 1.0 [MMOL)] were dissolved in water (2 mL) and to the solution were added aqueous formaldehyde (82 [UL,] 1.0 [MMOL)] and deazaguanine (120 mg, 0.8 [MMOL).] The reaction was stirred at 95 C for 12 h. Silica ge . (1.0 g) was added and the mixture was evaporated to dryness. Purification by chromatography on silica gel, using CH2CI2 : MeOH : [NH40H] (5: 4: 1) as the eluent, afforded n as the acetic acid salt. After conversion to the HCI salt and 1H and 13C. NMR spectra analysis, the compound was found to be identical in all respects with that previously reported (Evans, G. B.; Furneaux, R. H.; Lewandowicz, A.; Schramm, V. L. ; [TYLER,. P.] C. J. Med. [CHEM.,] in press.)
With sodium hydroxide; tetrabutylammomium bromide; In dichloromethane; water; at 0 - 20℃; for 2h;
2-Amino-5-benzyl-3H-pyrroIo[3,2-</]pyrimidin-4(5H)-oneTo a suspension of 2-amino-3H-pyrrolo[3,2-J]pyrimidin-4(5H)-one (336.7 mg, 2.0 mmol) in CH2Cl2 (14.3 mL) was added benzyl bromide (0.26 mL, 2.2 mmol) and TBABr (644 mg, 2.0 mmol). The reaction mixture was cooled to 0 0C, and to it was added 50% NaOH (1.7 mL). The resulting mixture was stirred for 2 h as it warmed from 0 0C to room temperature. Water was then added, and the solution was washed with CHCl3. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. Purification by column chromatography, eluting with CH2C12/Acetone (5:1-1 : 1), afforded the product as a tan solid (423 mg, 82%)
With ammonium formate;palladium 10% on activated carbon; In methanol; at 75℃; for 4h;
2-Amino-3H-pyrrolo[3,2-</]pyrimidm-4(5H)-one To a mixture of 2-amino-3-benzyl-3H-pyrrolo[3,2-(f]pyrimidin-4(5H)-one (10 g, 0.04 mol) in MeOH (334 mL) was added 10% Pd/C (2 g), ammonium formate (13.2 g, 0.21 mmol) and heated at 750C for 4 h. After completion of the reaction, the reaction mixture was cooled and filtered through a pad of Celite with hot 1 : 1 DMF/MeOEta. The filtrate was concentrated in vacuo to provide the product as an off-white solid (6.2 g, 99%).
2-amino-3H,5H-7-(4-fluorbenzoyl)pyrrolo[3,2-d]pyrimidin-4-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
64%
General procedure: Amixture of 9-deazapurine 5 (150.0 mg, 1.0 mmol) and benzoylchloride (2.2 equiv) in trifluoromethanesulfonic acid (3.45 g,23 mmol) was stirred at 80-120 C for 48 h. After the mixturewas cooled and H2O (15 mL) was added. Then the reaction wasneutralized with NaOH 1.0 mol/L, the volume adjusted to approximately35 mL by adding H2O and then 60 equiv of NaOH wereadded. The reaction was stirred for 2.5 h at 60 C. The mixturewas neutralized with glacial acetic acid and the formed solid wasfiltered under vacuum and washed several times with dichloromethane(10 mL), ethyl acetate (10 mL), acetone (5 mL) andmethanol (5 mL). The precipitate purity was monitored by CCDand depending on the product, further purification was necessaryby recrystallization in methanol or flash chromatography usingCH2Cl2/MeOH (4:1) as eluent.
2-amino-3H,5H-7-(4-chlorobenzoyl)pyrrolo[3,2-d]pyrimidin-4-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
68%
General procedure: Amixture of 9-deazapurine 5 (150.0 mg, 1.0 mmol) and benzoylchloride (2.2 equiv) in trifluoromethanesulfonic acid (3.45 g,23 mmol) was stirred at 80-120 C for 48 h. After the mixturewas cooled and H2O (15 mL) was added. Then the reaction wasneutralized with NaOH 1.0 mol/L, the volume adjusted to approximately35 mL by adding H2O and then 60 equiv of NaOH wereadded. The reaction was stirred for 2.5 h at 60 C. The mixturewas neutralized with glacial acetic acid and the formed solid wasfiltered under vacuum and washed several times with dichloromethane(10 mL), ethyl acetate (10 mL), acetone (5 mL) andmethanol (5 mL). The precipitate purity was monitored by CCDand depending on the product, further purification was necessaryby recrystallization in methanol or flash chromatography usingCH2Cl2/MeOH (4:1) as eluent.
2-amino-3H,5H-7-(4-bromobenzoyl)pyrrolo[3,2-d]pyrimidin-4-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
65%
General procedure: Amixture of 9-deazapurine 5 (150.0 mg, 1.0 mmol) and benzoylchloride (2.2 equiv) in trifluoromethanesulfonic acid (3.45 g,23 mmol) was stirred at 80-120 C for 48 h. After the mixturewas cooled and H2O (15 mL) was added. Then the reaction wasneutralized with NaOH 1.0 mol/L, the volume adjusted to approximately35 mL by adding H2O and then 60 equiv of NaOH wereadded. The reaction was stirred for 2.5 h at 60 C. The mixturewas neutralized with glacial acetic acid and the formed solid wasfiltered under vacuum and washed several times with dichloromethane(10 mL), ethyl acetate (10 mL), acetone (5 mL) andmethanol (5 mL). The precipitate purity was monitored by CCDand depending on the product, further purification was necessaryby recrystallization in methanol or flash chromatography usingCH2Cl2/MeOH (4:1) as eluent.
2-amino-3H,5H-7-(4-iodobenzoyl)pyrrolo[3,2-d]pyrimidin-4-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
56%
General procedure: Amixture of 9-deazapurine 5 (150.0 mg, 1.0 mmol) and benzoylchloride (2.2 equiv) in trifluoromethanesulfonic acid (3.45 g,23 mmol) was stirred at 80-120 C for 48 h. After the mixturewas cooled and H2O (15 mL) was added. Then the reaction wasneutralized with NaOH 1.0 mol/L, the volume adjusted to approximately35 mL by adding H2O and then 60 equiv of NaOH wereadded. The reaction was stirred for 2.5 h at 60 C. The mixturewas neutralized with glacial acetic acid and the formed solid wasfiltered under vacuum and washed several times with dichloromethane(10 mL), ethyl acetate (10 mL), acetone (5 mL) andmethanol (5 mL). The precipitate purity was monitored by CCDand depending on the product, further purification was necessaryby recrystallization in methanol or flash chromatography usingCH2Cl2/MeOH (4:1) as eluent.
2-amino-3H,5H-7-(3-fluorobenzoyl)pyrrolo[3,2-d]pyrimidin-4-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
71%
General procedure: Amixture of 9-deazapurine 5 (150.0 mg, 1.0 mmol) and benzoylchloride (2.2 equiv) in trifluoromethanesulfonic acid (3.45 g,23 mmol) was stirred at 80-120 C for 48 h. After the mixturewas cooled and H2O (15 mL) was added. Then the reaction wasneutralized with NaOH 1.0 mol/L, the volume adjusted to approximately35 mL by adding H2O and then 60 equiv of NaOH wereadded. The reaction was stirred for 2.5 h at 60 C. The mixturewas neutralized with glacial acetic acid and the formed solid wasfiltered under vacuum and washed several times with dichloromethane(10 mL), ethyl acetate (10 mL), acetone (5 mL) andmethanol (5 mL). The precipitate purity was monitored by CCDand depending on the product, further purification was necessaryby recrystallization in methanol or flash chromatography usingCH2Cl2/MeOH (4:1) as eluent.
2-amino-3H,5H-7-(3-chlorobenzoyl)pyrrolo[3,2-d]pyrimidin-4-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
73%
General procedure: Amixture of 9-deazapurine 5 (150.0 mg, 1.0 mmol) and benzoylchloride (2.2 equiv) in trifluoromethanesulfonic acid (3.45 g,23 mmol) was stirred at 80-120 C for 48 h. After the mixturewas cooled and H2O (15 mL) was added. Then the reaction wasneutralized with NaOH 1.0 mol/L, the volume adjusted to approximately35 mL by adding H2O and then 60 equiv of NaOH wereadded. The reaction was stirred for 2.5 h at 60 C. The mixturewas neutralized with glacial acetic acid and the formed solid wasfiltered under vacuum and washed several times with dichloromethane(10 mL), ethyl acetate (10 mL), acetone (5 mL) andmethanol (5 mL). The precipitate purity was monitored by CCDand depending on the product, further purification was necessaryby recrystallization in methanol or flash chromatography usingCH2Cl2/MeOH (4:1) as eluent.
2-amino-3H,5H-7-(2-chlorobenzoyl)pyrrolo[3,2-d]pyrimidin-4-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
61%
General procedure: Amixture of 9-deazapurine 5 (150.0 mg, 1.0 mmol) and benzoylchloride (2.2 equiv) in trifluoromethanesulfonic acid (3.45 g,23 mmol) was stirred at 80-120 C for 48 h. After the mixturewas cooled and H2O (15 mL) was added. Then the reaction wasneutralized with NaOH 1.0 mol/L, the volume adjusted to approximately35 mL by adding H2O and then 60 equiv of NaOH wereadded. The reaction was stirred for 2.5 h at 60 C. The mixturewas neutralized with glacial acetic acid and the formed solid wasfiltered under vacuum and washed several times with dichloromethane(10 mL), ethyl acetate (10 mL), acetone (5 mL) andmethanol (5 mL). The precipitate purity was monitored by CCDand depending on the product, further purification was necessaryby recrystallization in methanol or flash chromatography usingCH2Cl2/MeOH (4:1) as eluent.
2-amino-3H,5H-7-(2,4,6-trichlorobenzoyl)pyrrolo[3,2-d]pyrimidin-4-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
52%
General procedure: Amixture of 9-deazapurine 5 (150.0 mg, 1.0 mmol) and benzoylchloride (2.2 equiv) in trifluoromethanesulfonic acid (3.45 g,23 mmol) was stirred at 80-120 C for 48 h. After the mixturewas cooled and H2O (15 mL) was added. Then the reaction wasneutralized with NaOH 1.0 mol/L, the volume adjusted to approximately35 mL by adding H2O and then 60 equiv of NaOH wereadded. The reaction was stirred for 2.5 h at 60 C. The mixturewas neutralized with glacial acetic acid and the formed solid wasfiltered under vacuum and washed several times with dichloromethane(10 mL), ethyl acetate (10 mL), acetone (5 mL) andmethanol (5 mL). The precipitate purity was monitored by CCDand depending on the product, further purification was necessaryby recrystallization in methanol or flash chromatography usingCH2Cl2/MeOH (4:1) as eluent.
With sodium hydroxide; In water; for 0.25h;Microwave irradiation;
In the sequence, in a microwave tube was added 4 (200 mg,0.97 mmol) and NaOH (195.0 mg, 4.84 mmol) in H2O (5 mL). Theset conditions were 95 C for 15 min with an average power of40 W. This procedure was repeated four times and then the crudeproducts were mixed. The solvent was evaporated under vacuumand then water (5 mL) was added. The mixture was acidified topH 5.0 with glacial acetic acid. The precipitate was filtered andthen recrystallized in ethanol/H2O (3:1) affording the desired product5 in 96% yield (701.0 mg)
2-O-methyl-1,3,5-tri-O-benzoyl-β-D-ribofuranose[ No CAS ]
[ 65996-58-9 ]
C26H24N4O7[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
30%
With tin(IV) chloride; In nitromethane; at 60℃; for 0.5h;
To a suspension of <strong>[65996-58-9]2-amino-5H-pyrrolo[3,2-d]pyrimidin-4(3H)-one</strong> (<strong>[65996-58-9]9-deazaguanine</strong>) (0.454 g, 3.0 mmol) (prepared according to J. Org. Chem. 1978, 43, 2536) and 2-O-methyl-1,3,5-tri-O-benzoyl-beta-D-ribofuranose (1.54 g, 3.2 mmol) in dry nitromethane (23 mL) at 60 C. was added stannic chloride (0.54 mL, 4.5 mmol). The reaction mixture was maintained at this temperature for 0.5 hr., cooled and poured onto ice-cold saturated sodium bicarbonate solution (70 mL). The insoluble material was filtered through florisil and washed with ethyl acetate (3×50 mL). The filtrate was extracted with ethyl acetate (2×50 mL), and organic layer was washed with water (2×50 mL), dried over Na2SO4 and evaporated to dryness. Chromatography of the resulting foam on silica gel with CH2Cl2/ MeOH (14:1) afforded the benzoylated product (0.419 g, 30% yield). To a suspension of the benzoylated product (0.25 g) in MeOH (2.4 mL) was added t-butylamine (0.52 mL) and stirring at room temperature was continued for 24 hrs. followed by addition of more t-butylamine (0.2 mL). The reaction mixture was stirred at ambient temperature overnight, concentrated in vacuum and the residue was purified by flash chromatography over silica gel using CH2Cl2/MeOH (85:15) as eluent giving the desired compound as a foam (0.80 g).
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