ethyl 3-(furan-2-yl)-2-methyl-3-oxopropanoate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-furan-2-yl-2-methyl-3-oxo-propionic acid ethyl ester (49 mg) was added sodium ethoxide (0.22 ml) and 0.5 ml ethanol. A solid precipitates. The solution was stirred at room temperature for 1 h, iodomethane was added and the suspension stirred at room temperature for 3 h. Concentration in vacuo and purification by HPLC gave the expected product. A solid precipitates iodomethane was added the suspension stirred at room temperature for 3 h Concentration in vacuo and purification by HPLC

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-furan-2-yl-2-methyl-3-oxo-propionic acid ethyl ester (49 mg) and 4-Hydrazino-N-(1,2,2,6,6-pentamethyl-piperidin-4-yl)-benzamide (85 mg) in 0.5 ml of acetic acid were heated up at 65° C. for 2 h. Concentration in vacuo and purification by HPLC gave the expected product. MH+=437.3 Concentration in vacuo and purification by HPLC

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a flask were placed ethyl 3-(2-furyl)-3-oxopropanoate (0.5 g), iodomethane (0.14 ml), finely ground potassium carbonate (0.75 g) and acetone (5 ml). The mixture was stirred at reflux for 2 h. A further portion of iodomethane (0.9 mmol, 0.056 ml) and potassium carbonate (0.9 mmol, 0.12 g) were added and the mixture stirred at reflux for 1 h. The reaction mixture was filtered and concentrated under vacuum. Yield (0.5 g, 93%). In a flask were placed at reflux for 2 h the mixture stirred at reflux for 1 h The reaction mixture was filtered concentrated under vacuum Yield (0.5 g, 93%)

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following the method of Rorig and Nicholson (U.S. Pat. No. 2,710,867), a mixture of 3.00 g (15.3 mmol) (RS)-3-furan-2-yl-2-methyl-3-oxo-propionic acid ethyl ester and 1,38 g (7.65 mmol) guanidine carbonate in 20 ml ethanol was heated at 100° C. for 16 hours. The reaction mixture was then cooled to 0° C., whereupon the resulting crystals were collected by filtration and washed sequentially with water and with ice-cold ethanol to afford 1.80 g (62%) 2-amino-6-furan-2-yl-5-methyl-3H-pyrimidin-4-one as a white crystalline solid. ES-MS m/e (%): 190 ([M—H]−, 100). The reaction mixture was then cooled to 0° C., whereupon the resulting crystals were collected by filtration washed sequentially with water and with ice-cold ethanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 5.0 g (27.4 mmol) ethyl beta-oxo-2-furanpropionate in 15 ml dry THF under argon at −78° C. was added dropwise 27.4 ml (27.4 mmol, 1M solution in THF) lithium bis(trimethylsilyl)amide and stirring continued for 15 minutes at −78° C. 5.44 ml (87.4 mmol) methyl iodide was then added dropwise and stirring continued for 30 minutes at −78° C., 2.5 hours at 0° C. and 20 hours at room temperature. The reaction mixture was poured into 100 ml 1M hydrochloric acid at 0° C. and the phases separated. The aqueous phase was extracted twice with ether and the combined organic extracts washed with brine, dried over sodium sulfate, and concentrated in vacuo. Chromatography (ethyl acetate/hexane 1/3) afforded 4.42 g (82%) (RS)-3-furan-2-yl-2-methyl-3-oxo-propionic acid ethyl ester as a yellow oil. EI-MS m/e (%): 196 (M+, 10), 168 ([M—C2H4]+, 6), 151 ([M—OEt]+, 7), 95 (100). stirring continued for 30 minutes at −78° C., 2.5 hours at 0° C. and 20 hours at room temperature the phases separated The aqueous phase was extracted twice with ether the combined organic extracts washed with brine dried over sodium sulfate concentrated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-furan-2-yl-2-methyl-3-oxo-propionic acid ethyl ester (49 mg) was added sodium ethoxide (0.22 ml) and 0.5 ml ethanol. A solid precipitates. The solution was stirred at room temperature for 1 h, iodomethane was added and the suspension stirred at room temperature for 3 h. Concentration in vacuo and purification by HPLC gave the expected product. A solid precipitates iodomethane was added the suspension stirred at room temperature for 3 h Concentration in vacuo and purification by HPLC

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-furan-2-yl-2-methyl-3-oxo-propionic acid ethyl ester (49 mg) and 4-Hydrazino-N-(1,2,2,6,6-pentamethyl-piperidin-4-yl)-benzamide (85 mg) in 0.5 ml of acetic acid were heated up at 65° C. for 2 h. Concentration in vacuo and purification by HPLC gave the expected product. MH+=437.3 Concentration in vacuo and purification by HPLC

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a flask were placed ethyl 3-(2-furyl)-3-oxopropanoate (0.5 g), iodomethane (0.14 ml), finely ground potassium carbonate (0.75 g) and acetone (5 ml). The mixture was stirred at reflux for 2 h. A further portion of iodomethane (0.9 mmol, 0.056 ml) and potassium carbonate (0.9 mmol, 0.12 g) were added and the mixture stirred at reflux for 1 h. The reaction mixture was filtered and concentrated under vacuum. Yield (0.5 g, 93%). In a flask were placed at reflux for 2 h the mixture stirred at reflux for 1 h The reaction mixture was filtered concentrated under vacuum Yield (0.5 g, 93%)