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With copper(l) iodide; TPGS-450-M; caesium carbonate In water at 20℃; for 12 h; Inert atmosphere; Green chemistry
General procedure: A two-neck round bottom flask was charged with a magnetic stirrer, evacuated and backfilled with nitrogen. Substituted 2-halobenzoic acid (1, 0.5 mmol) and amidine hydrochloride (2, 0.75 mmol) or bis(guanidine) sulphate (2, 0.38 mmol) in 2 wt percent TPGS-750-M (3 mL) were added under nitrogen atmosphere. After a 10-min stirring, Cs2CO3 (1 mmol, 326 mg) was added to the flask. 15 min later, CuI (0.1 mmol, 19 mg) was added to the flask. The mixture was allowed to stir under nitrogen atmosphere at the shown temperature for 12 h (see Table 3 in text). After completion of the reaction, the mixture was extracted with EtOAc (1 mL), and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using petroleum ether/ethyl acetate (3:1 to 1:1) as eluent to provide the desired product.
With sodium ethanolate; In ethanol; for 6h;Heating / reflux; Argon atmosphere;
745mg, 5.17mmol) was dissolved in ethanol (15ml). Acetamidine hydrochloride (489mg, 5.17mmol) and sodium ethoxide in ethanol (0.41ml, 5.17mmol) were added and the mixture heated under argon at reflux for 6 hours and then overnight. The solvent was evaporated and the residue was treated with water (50ml) and extracted with diethyl EPO <DP n="34"/>ether (4 x 30ml). The diethyl ether layers were combined, dried over magnesium sulphate, filtered and evaporated. The crude product was purified using silica gel chromatography, eluting with a mixture of ethyl acetate and pentane (20-50percent) to afford the product (D33); MS (ES+) m/e 167 [M+H]+.
Acetamidine hydrochloride (413 mg, 4.4 mmol) was added to a solution of sodium ethoxide (594 mg, 2.0 equiv.) in ethanol (8 mL). After stirring for half an hour at room temperature, the resultant sodium chloride was removed by filtration. The filtrate was added to ethyl 2-cyano- 4,4-diethoxybutanoate (1.0 g, 4.4 mmol) and the mixture was refluxed for 5 hours. Most of the solvent was removed and the remaining slurry was <n="73"/>dissolved in ice water, and extracted with ethyl acetate. The extracts were washed with brine, dried over MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography on silica gel (100percent methanol). The desired product was obtained as a red solid (421 mg, 40percent). MS: (M + H)/z = 242.
6-chloro-2-methylpyrido[3,4-d]pyrimidin-4(3H)-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
86%
With sodium acetate; In 2-methoxy-ethanol; at 120℃; for 6h;
The compound <strong>[58483-95-7]5-amino-2-chloropyridine-4-carboxylic acid</strong> (1000 g, 5.8 mol) was dissolved in 5000 ml of ethylene glycol monomethyl ether and acetamidine hydrochloride (2193 g, 23.2 mol) Sodium (2360 g, 17.4 mol). The reaction was heated to 120 ° C for 6 hours. After the reaction was complete, the reaction was cooled to room temperature, poured into 4000 ml of water and extracted twice with ethyl acetate. The organic phase was combined, dried and concentrated to afford the crude product which was filtered to give 6-chloro- Pyridine [3,4-d] pyrimidin-4 (3 H) -one (976 g, 5.01 mol)
tert-butyl 4-hydroxy-2-methyl-5H,6H, 7H-pyrrolo[3,4-d]pyrimidine-6-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With triethylamine; In tert-butyl alcohol;Reflux;
A mixture of 1-tert-butyl 3-ethyl 4-oxopyrrolidine-l,3-dicarboxylate (CAS 146256-98-6) (20 g, 78 mmol), acetamidine hydrochloride (7.35 g, 78 mmol), and triethylamine (28.2 mL, 202 mmol) in tert-butanol (100 mL) was heated under reflux overnight. The reaction mixture was cooled to RT and concentrated in vacuo. The residue was partitioned between EtOAc and water. The organic layer was dried (phase separator) and concentrated in vacuo. The crude product was purified by column chromatography on silica, eluting with 0-15 percent MeOH in EtOAc to afford the title compound. H NMR (400 MHz, DMSO- 6): delta ppm 1.42 - 1.47 (m, 9H), 2.31 (s, 3H), 4.25 - 4.39 (m, 4H), 12.52 (br s, 1H). MS ES+ 252
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