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Example 109; Synthesis of 2- (6-Arnino-8-methyl-vurin-9-yl)-5-hydroxMeLhyl-tetrahvdro- furan-3, 4-diol; Step 1; Synthesis of 8-Methyl-9H-purin-6-ylamine; 4,5, 6-Triaminopyrimidine sulfate (3. 0g, 13.4mmol) and acetamide (l. Og, 16. 9mmol) were added to a 25mL autoclave bomb and heated to 240C for 6 hours. The crude product was then boiled in H20 for 1 hour and filtered through a small pad of Celite. The flow through was concentrated and purified by HPLC 0-10% Buffer B over 30min at a flow rate of lOmLs/min. Buffer A-0. 1% triethylammonium acetate in water, Buffer B-0. 1 % triethylammonium acetate in CH3CN. Pooled the appropriate fractions and concentrated in vacuo to give 225mg (11 %) of the title compound.
In methanol; dichloromethane; for 24.0h;Heating / reflux;
Step 2; Synthesis of N, N-Dimethyl-N'- (8-methyl-9H-purin-6-yl)-formamidine; To a suspension of the product in Step 1 above (225mg, 1. 5 lmmol) in MeOH (14mL) and methylene chloride (7mL) was added N'N'-dimethylformamide dimethyl acetal (0. 8mL, 4. 52mmol) and the mixture heated to reflux for 24 hours. The resuling yellow solution was concentrated in vacuo to a yellow oil. This oil was co- evaporated with methylene chloride (2 x 15mL) and held under high vacuum for 2hours. The crude product was used directly in Step 3, without further purification.
9-(2,3-di-O-acetyl-5-O-benzoyl-4-C-methyl-β-D-ribofuranosyl)-8-methyl adenine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With tin(IV) chloride; In acetonitrile; at 20.0℃;
dry acetonitrile (50 mL) solution of 7 (1.10g,2.79mmol) was treated with 8-methyl adenine and stannic chloride (SnCl4,660L,5.58mmol), and stirred at room temperature overnight. The solution wasconcentrated under reduced pressure, and diluted with chloroform (100 mL), andtreated with cold saturated aqueous NaHCO3 solution (100 mL). Themixture was filtered through Celite and the precipitate was washed with hot chloroform.The combined filtrates were washed with water (100 mL) and brine (100 mL), and dried(Na2SO4), and evaporated under reduced pressure. Theresidue was purified by silica gel column chromatography [eluent: methanol (3%to 5%) / step gradient of methylene chloride] to give 20
(1R,3S)-methyl 3-(methylsulfonyloxy)cyclopentanecarboxylate[ No CAS ]
[ 22387-37-7 ]
(1R,3R)-methyl 3-(6-amino-8-methyl-9H-purin-9-yl)cyclopentanecarboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
35.2%
With caesium carbonate; In N,N-dimethyl-formamide; at 80.0℃; for 5.0h;
Example 16-Preparation of (1R,3R)-methyl 3-(6-amino-8-methyl-9H-purin-9-yl)cyclopentanecarboxylate (Compound 9o) <strong>[22387-37-7]8-Methyladenin</strong>e (compound 80o, 200 mg, 1.3409 mmoles) and compound 5 (387 mg, 1.743 mmoles) were dissolved in anhydrous N,N-dimethylformamide (5 mL) and cesium carbonate (437 mg, 1.3409 mmoles) was added. The resulting mixture was stirred at 80 deg C. for 5 hours. After cooling to room temperature, the mixture was filtered and concentrated to dryness. Purification on basic alumina (1% methanol in dichloromethane) gave compound 9o (130 mg, 35.2% yield) as an off-white solid. 1HNMR (500 MHz, DMSO-d6) delta ppm: 8.1 (s, 1H), 7.0 (brs, 2H), 4.9 (m, 1H), 3.7-3.6 (s, 6H), 3.2 (m, 1H), 2.4-2.2 (m, 6H): Mass (m/z): 276.5 (M+H).
3-(2,6-dichloro-benzyl)-8-methyl-3H-purin-6-ylamine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
5%
In N,N-dimethyl-formamide; at 85.0℃;
A mixture of <strong>[22387-37-7]8-methyl-9H-purin-6-ylamine</strong> (150 mg, 1.0 mmol) and l,3-dichloro-2- chloromethyl-benzene (214 mg, 1.1 mmol) in DMF (3 mL) was stirred at 85 C overnight. The mixture was cooled and filtered. The filtrate was purified by prep-HPLC (NH4HCO3 system) to give 3-(2,6-dichloro-benzyl)-8-methyl-3H-purin-6-ylamine (2 mg, yield: 5 %) as white solid. 1H NMR (400 MHz, DMSO- d): d = 7.82 (s, 1H), 7.70 (brs, 2H), 7.60-7.58 (m, 2H), 7.51-7.47 (m, 1H), 5.67 (s, 2H), 2.38 (s, 3H). MS: m/z 308.0 (M+H+).
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; at 95.0℃;Inert atmosphere;
A flask charged with 8-bromo-9H-purin-6-ylamine (500 mg, 2.3 mmol), methylboronic (200 mg, 3.5mmol), Pd(dppf)Cl2 (84 mg, 0.115 mmol) and K2C03 (938 mg, 0.9 mmol) in dioxane/H20 (50 mL/l0 mL) was degassed and filled with N2. The mixture was stirred at 95 C overnight. Solvent was removed and the residue was purified with prep-TLC (DCM/MeOH = 10/1) to give 8-methyl-9H-purin-6-ylamine (150 mg, yield: 43 %) as yellow solid. MS: m/z 150.0 (M+H+).
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