2-(furan-2-yl)ethanamine

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: 3.2 g of 2-(2-aminoethyl)-furan are dissolved in 45 ml of pyridine and at 5° C. a solution of 8.8 g of benzenesulphonic acid chloride in 50 ml of pyridine is added. The resulting mixture is then stirred overnight at ambient temperature, the reaction product is evaporated down, the residue is taken up in water and extracted with methylene chloride. After the organic phase has been dried over magnesium sulphate the solution is concentrated by evaporation and chromatographed over a silica gel column using ethylene chloride. is added the reaction product is evaporated down extracted with methylene chloride After the organic phase has been dried over magnesium sulphate the solution is concentrated by evaporation chromatographed over a silica gel column

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

Procedure: 3.2 g of 2-(2-aminoethyl)-furan are dissolved in 45 ml of pyridine and at 5° C. a solution of 8.8 g of benzenesulphonic acid chloride in 50 ml of pyridine is added. The resulting mixture is then stirred overnight at ambient temperature, the reaction product is evaporated down, the residue is taken up in water and extracted with methylene chloride. After the organic phase has been dried over magnesium sulphate the solution is concentrated by evaporation and chromatographed over a silica gel column using ethylene chloride. is added the reaction product is evaporated down extracted with methylene chloride After the organic phase has been dried over magnesium sulphate the solution is concentrated by evaporation chromatographed over a silica gel column

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

Procedure: A solution of 10 gm (0.082 mol) of furfurylmethylamine in 50 ml of ethanol and 10 gm of triethylamine was mixed with 17 gm of p-methylphenacylbromide and stirred for two hours. The triethylamine hydrochloride precipitated was subjected to suction filtration. The mother liquor was mixed with 4 gm of sodium borohydride and stirred for one hour at ambient temperature. Then, water was added, and the mixture was extracted with ether. The ether solution was dried, and the ether was distilled off in vacuo. The 2-furfuryl-2-methylamino-1-p-methylphenyl ethanol was left behind in the form of an oil. The triethylamine hydrochloride precipitated was subjected to suction filtration The mother liquor was mixed with 4 gm of sodium borohydride stirred for one hour at ambient temperature Then, water was added the mixture was extracted with ether The ether solution was dried the ether was distilled off in vacuo The 2-furfuryl-2-methylamino-1-p-methylphenyl ethanol was left behind in the form of an oil

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

Procedure: 2-(furan-2-yl)ethanamine (0.81 g, 7.30 mmol) was added to a premixed (10 min) solution of 3-tert-butyl-1H-pyrazole-5-carboxylic acid (0.61 g, 3.60 mmol), DCC (1.51 g, 7.30 mmol) and HOBt (0.99 g, 7.30 mmol) in DCM:DMF-solution (10 ml, 2:9, v/v). After stirring for 15 h at RT the reaction mixture was filtered through a pad of Celite and the filtrate was washed two times with water, evaporated to dryness and purified with CombiFlash to afford 0.36 g of the title compound. 1H-NMR (400 MHz; d6-DMSO): δ 1.27 (s, 9H), 2.84 (t, 2H), 3.46 (m, 2H), 6.17 (m, 1H), 6.35 (m, 2H), 7.52 (m, 1H), 8.08 (m, 1H), 12.89 (m, 1H). was filtered through a pad of Celite the filtrate was washed two times with water evaporated to dryness purified with CombiFlash

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

Procedure: Here, 2-(2-amino-ethyl)furan (10.0 g, 0.090 mol) is refluxed with ethyl formate (80 ml, 1.0 mol) for 12 hours. The reaction product is concentrated by evaporation and distilled in vacuo. The reaction product is concentrated by evaporation distilled in vacuo

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

Procedure: Here, 2-(2-amino-ethyl)furan (10.0 g, 0.090 mol) is refluxed with ethyl formate (80 ml, 1.0 mol) for 12 hours. The reaction product is concentrated by evaporation and distilled in vacuo. The reaction product is concentrated by evaporation distilled in vacuo

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

Procedure: In close analogy to the procedure described above, 2-Furan-2-yl-ethylamine is reacted with acetic anhydride to provide the title compound.

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

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 5-bromo-2-chloro-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidine (Method 1; 290 mg, 11.0 mmol), 2-(2-aminoethyl)furan (330 mg, 3.0 mmol) and 1-butanol (5 ml) was heated at 120° C. for 5 hours. The mixture was allowed to cool to ambient temperature and the volatiles removed by evaporation. The residue was dissolved in DCM and washed with water followed by brine. The organics were separated, dried (MgSO4) and the solvent removed by evaporation. The residue was triturated with ether, the solid product collected and purified by column chromatography on silica gel eluting with DCM/methanol (95:5) to give the titled compound (80 mg, 22%). 1H NMR (DMSO): δ 2.1 (s, 3H), 2.85 (m, 2H), 3.45 (m 2H), 6.10 (m, 1H), 6.35 (m, 1H), 6.4 (br s, 1H), 7.15 (br s, 1H), 7.5 (s, 1H), 8.0 (br s, 2H), 12.05 (br s, 1H); MS: m/z 363. to cool to ambient temperature the volatiles removed by evaporation The residue was dissolved in DCM washed with water The organics were separated dried (MgSO4) the solvent removed by evaporation The residue was triturated with ether the solid product collected purified by column chromatography on silica gel eluting with DCM/methanol (95:5)

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

Procedure: 3.7 g (46 mmole) of a 37% aqueous formaldehyde solution were added dropwise at room temperature to 5.1 g (46 mmole) of 2-furylethylamine [the compound described, for example, in Brit., J. Pharmacol., 9, 376 (1954)], and the resulting mixture was stirred for about 15 minutes, after which it was extracted with diethyl ether. The organic extract was washed with water and dried over anhydrous sodium sulfate, and then the diethyl ether was removed by distillation under reduced pressure. 5 ml of dimethylformamide were added to the residue, and the resulting solution was added dropwise to 15 ml of dimethylformamide containing 3.6 g (100 mmole) of dry hydrogen chloride at room temperature. The resulting mixture was then stirred for 3 hours. At the end of this time, the greater part of the dimethylformamide was removed by distillation under reduced pressure, and then water and a 0.1N aqueous solution of sodium hydroxide were added to the residue so as to adjust its pH to a value of about 11; the mixture was then extracted with chloroform. The organic extract was washed with water and dried over anhydrous sodium sulfate. The chloroform was then removed by evaporation under reduced pressure, and the resulting residue was purified by silica gel column chromatography, using a 50:1 by volume mixture of chloroform and methanol as the eluent, to give the title compound as a brown oil in a yield of 27%. after which it was extracted with diethyl ether The organic extract was washed with water dried over anhydrous sodium sulfate the diethyl ether was removed by distillation under reduced pressure 5 ml of dimethylformamide were added to the residue The resulting mixture was then stirred for 3 hours At the end of this time, the greater part of the dimethylformamide was removed by distillation under reduced pressure water and a 0.1N aqueous solution of sodium hydroxide were added to the residue so as the mixture was then extracted with chloroform The organic extract was washed with water dried over anhydrous sodium sulfate The chloroform was then removed by evaporation under reduced pressure the resulting residue was purified by silica gel column chromatography by volume mixture of chloroform and methanol as the eluent