1-(furan-2-yl)butane-1,3-dione

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

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

Procedure: A mixture of methyl 2-furoate (23 g, 0.18 mole) and acetone (10.6 g, 0.18 mole) was slowly added to a stirred suspension of potassium tert-butoxide (41 g, 0.36 mole) in anhydrous toluene (300 ml) at 0° C. Upon standing overnight at room temperature, glacial acetic acid (22 ml, 0.36 mole) and then water (100 ml) were added. The organic layer was separated, combined with an ether extract of the aqueous phase, washed with water, dried, and distilled to give 1-(2-furyl)-1,3-dioxobutane: b.p. 66°-70° C./0.1 mm (18.5 g). The organic layer was separated extract of the aqueous phase washed with water dried distilled

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

Procedure: Was prepared according to Example 9 from (4-chloro-phenyl)-(2-hydrazino-9-methyl-9H-purin-6-yl)-amine and 1-(2-furyl)-1,3-butanedione. Was prepared

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

Procedure: A mixture of methyl 2-furoate (23 g, 0.18 mole) and acetone (10.6 g, 0.18 mole) was slowly added to a stirred suspension of potassium tert-butoxide (41 g, 0.36 mole) in anhydrous toluene (300 ml) at 0° C. Upon standing overnight at room temperature, glacial acetic acid (22 ml, 0.36 mole) and then water (100 ml) were added. The organic layer was separated, combined with an ether extract of the aqueous phase, washed with water, dried, and distilled to give 1-(2-furyl)-1,3-dioxobutane: b.p. 66°-70° C./0.1 mm (18.5 g). The organic layer was separated extract of the aqueous phase washed with water dried distilled

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

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

Procedure: The title compound was prepared (as described above for the preparation of Example 2) from 630 mg (1.31 mmol) of Intermediate 45 (as the TFA salt) and 200 mg (1.31 mmol) of 1-(2-furyl)-1,3-butadione (purchased from Acros Organics) to yield 230 mg (35% yield) of Example 29 as a light brown solid: TLC (DCM/MeOH (4:1): Rf=0.62; 1H NMR (DMSO-d6, 300 MHz) δ11.07 (d, 1H, J=8.7), 7.88 (m, 2H), 7.69 (d, 1H, J=1.0), 7.48 (m, 3H), 7.09 (d, 2H, J=8.5), 6.86 (m, 3H), 6.52 (d, 1H, J=1.5), 5.33 (s, 1H), 4.13 (t, 2H, J=6.6), 4.03 (m, 1H), 3.14 (m, 1H), 2.87 (t, 2H, J=6.6), 2.70 (dd, 1H, J=13.6, 9.0), 2.34 (s, 3H), 1.62 (s, 3H); low resolution MS (ES+)m/e 501.2 (MH+).

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

Procedure: A solution of 410 mg (1.95 mmol) N-(p-tolyl)-o-aminobenzaldehyde 326 mg (2.15 mmol), (2-furoyl)acetone and 50 mg piperidine in 4 ml 95% ethanol was heated overnight under reflux. Removal of he volatile materials left a black, gummy oil which was taken up in dichloromethane and, after being washed with 3M NaOH, brine, and dried (MgSO4), purified by flash chromatography [eluent, 3:2 pentane-diethyl ether (3:2)] yielding 355 mg (1.50 mmol, 77%) product. under reflux Removal of he volatile materials left a black, gummy oil which after being washed with 3M NaOH, brine dried (MgSO4) purified by flash chromatography [eluent, 3:2 pentane-diethyl ether (3:2)]

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

Procedure: A solution of 410 mg (1.95 mmol) N-(p-tolyl)-o-aminobenzaldehyde 326 mg (2.15 mmol), (2-furoyl)acetone and 50 mg piperidine in 4 ml 95% ethanol was heated overnight under reflux. Removal of he volatile materials left a black, gummy oil which was taken up in dichloromethane and, after being washed with 3M NaOH, brine, and dried (MgSO4), purified by flash chromatography [eluent, 3:2 pentane-diethyl ether (3:2)] yielding 355 mg (1.50 mmol, 77%) product. under reflux Removal of he volatile materials left a black, gummy oil which after being washed with 3M NaOH, brine dried (MgSO4) purified by flash chromatography [eluent, 3:2 pentane-diethyl ether (3:2)]

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

Procedure: A solution of 410 mg (1.95 mmol) N-(p-tolyl)-o-aminobenzaldehyde 326 mg (2.15 mmol), (2-furoyl)acetone and 50 mg piperidine in 4 ml 95% ethanol was heated overnight under reflux. Removal of he volatile materials left a black, gummy oil which was taken up in dichloromethane and, after being washed with 3M NaOH, brine, and dried (MgSO4), purified by flash chromatography [eluent, 3:2 pentane-diethyl ether (3:2)] yielding 355 mg (1.50 mmol, 77%) product. under reflux Removal of he volatile materials left a black, gummy oil which after being washed with 3M NaOH, brine dried (MgSO4) purified by flash chromatography [eluent, 3:2 pentane-diethyl ether (3:2)]

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

Procedure: 4.27 ml (5.04 g, 40 mmol) methyl 2-furoate was added to a suspension of NaH (made from 3.83 g commercial NaH slurry by removal of the mineral oil with pentane) in 30 ml anhydrous diethyl ether. To this was added, so as to maintain the temperature below 30° C., 5.87 ml (4.64 g, 80 mmol) acetone (dried over CaCl2). This mixture was heated under reflux for 2 h, cooled, and divided between diethyl ether and 3M HCl. The ether layer was washed with brine, dried (MgSO4), and concentrated to yield 6.06 g of a red oil (raw yield 99%) which was purified by vacuum distillation (b.p. 85°-90° C./1 torr). made from 3.83 g commercial NaH slurry by removal of the mineral oil with pentane) in 30 ml anhydrous diethyl ether To this was added This mixture was heated under reflux for 2 h cooled The ether layer was washed with brine dried (MgSO4) concentrated

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

Procedure: 4.27 ml (5.04 g, 40 mmol) methyl 2-furoate was added to a suspension of NaH (made from 3.83 g commercial NaH slurry by removal of the mineral oil with pentane) in 30 ml anhydrous diethyl ether. To this was added, so as to maintain the temperature below 30° C., 5.87 ml (4.64 g, 80 mmol) acetone (dried over CaCl2). This mixture was heated under reflux for 2 h, cooled, and divided between diethyl ether and 3M HCl. The ether layer was washed with brine, dried (MgSO4), and concentrated to yield 6.06 g of a red oil (raw yield 99%) which was purified by vacuum distillation (b.p. 85°-90° C./1 torr). made from 3.83 g commercial NaH slurry by removal of the mineral oil with pentane) in 30 ml anhydrous diethyl ether To this was added This mixture was heated under reflux for 2 h cooled The ether layer was washed with brine dried (MgSO4) concentrated

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

Procedure: 4.27 ml (5.04 g, 40 mmol) methyl 2-furoate was added to a suspension of NaH (made from 3.83 g commercial NaH slurry by removal of the mineral oil with pentane) in 30 ml anhydrous diethyl ether. To this was added, so as to maintain the temperature below 30° C., 5.87 ml (4.64 g, 80 mmol) acetone (dried over CaCl2). This mixture was heated under reflux for 2 h, cooled, and divided between diethyl ether and 3M HCl. The ether layer was washed with brine, dried (MgSO4), and concentrated to yield 6.06 g of a red oil (raw yield 99%) which was purified by vacuum distillation (b.p. 85°-90° C./1 torr). made from 3.83 g commercial NaH slurry by removal of the mineral oil with pentane) in 30 ml anhydrous diethyl ether To this was added This mixture was heated under reflux for 2 h cooled The ether layer was washed with brine dried (MgSO4) concentrated