2-(4-fluorophenoxy)ethanamine

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

Procedure: To 2-(4-Fluorophenoxy)ethylamine (27.4 mg, 0.18 mmol) was added a solution of (7-Hydroxy-5,6,7,8-tetrahydro-naphthalen-1-yl)-carbamic acid phenyl ester (50.0 mg, 0.18 mmol) in 1.5 mL dimethylsulfoxide. The mixture was stirred for 40 minutes, and then poured into water. The resulting solid was filtered and dried under reduced pressure (54.2 mg, 89.2% yield). The resulting solid was filtered dried under reduced pressure (54.2 mg, 89.2% yield)

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

Conditions: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-[(1S)-(1-phenylethyl)amino]-6-chloropyrimidine, (Intermediate III, Compound of Example 6), (234 mg, 1.0 mmole) and [2-(4-fluorophenoxy)ethyl]amine (357 mg, 2.3 mmole) were combined in a 2 mL pressure vial which was then securely capped. The vial was heated at 150° C. for 20 hours. After cooling, the solid mass was dissolved in CH2Cl2 (25 mL) and extracted with saturated sodium carbonate (25 mL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was recrystallized from CH2Cl2 (5 mL) to afford the titled compound as a white solid (191 mg, 54%). 1H NMR (CDCl3) δ 1.54 (d, J=6.6 Hz, 3H), 3.54 (q, J=5.5 Hz, 2H), 3.94 (t, J=5.5 Hz, 2H), 4.59 (p, J=6.6 Hz, 1H), 5.05 (broad m, 1H), 5.08 (s, 1H), 5.34 (broad d,1H), 6.77 (m, 2H), 6.95 (t, J=9.1 Hz, 2H), 7.23 (m,1H), 7.32 (d, J=4.4 Hz, 4H), 8.09 (s, 1H), LC/MS (MH+) m/e 353.79 obs. was then securely capped After cooling extracted with saturated sodium carbonate (25 mL) The organic layer was dried over sodium sulfate concentrated under reduced pressure The residue was recrystallized from CH2Cl2 (5 mL)

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

Procedure: To 2-(4-Fluorophenoxy)ethylamine (27.4 mg, 0.18 mmol) was added a solution of (7-Hydroxy-5,6,7,8-tetrahydro-naphthalen-1-yl)-carbamic acid phenyl ester (50.0 mg, 0.18 mmol) in 1.5 mL dimethylsulfoxide. The mixture was stirred for 40 minutes, and then poured into water. The resulting solid was filtered and dried under reduced pressure (54.2 mg, 89.2% yield). The resulting solid was filtered dried under reduced pressure (54.2 mg, 89.2% yield)

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

Procedure: To 2-(4-Fluorophenoxy)ethylamine (27.4 mg, 0.18 mmol) was added a solution of (7-Hydroxy-5,6,7,8-tetrahydro-naphthalen-1-yl)-carbamic acid phenyl ester (50.0 mg, 0.18 mmol) in 1.5 mL dimethylsulfoxide. The mixture was stirred for 40 minutes, and then poured into water. The resulting solid was filtered and dried under reduced pressure (54.2 mg, 89.2% yield). The resulting solid was filtered dried under reduced pressure (54.2 mg, 89.2% yield)

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

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

Procedure: Hydrazine solution (138 mg, 2.75 mmol) was added to a solution of 2-(2-(4-fluorophenoxy)ethyl)isoindoline-1,3-dione (713 mg, 2.5 mmol) in methanol (8 ml) and stirred at room temperature for 4 hours. The resulting solid was filtered off and concentrated in vacuo. The residue was triturated with diethyl ether (30 ml), and the resulting solid was filtered off again and concentrated in vacuo to give 2-(4-fluorophenoxy)ethanamine (280 mg, 70%) as colorless oil: LCMS: 325 [M+1]+. The resulting solid was filtered off concentrated in vacuo The residue was triturated with diethyl ether (30 ml) the resulting solid was filtered off again concentrated in vacuo

Conditions: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-[(1S)-(1-phenylethyl)amino]-6-chloropyrimidine, (Intermediate III, Compound of Example 6), (234 mg, 1.0 mmole) and [2-(4-fluorophenoxy)ethyl]amine (357 mg, 2.3 mmole) were combined in a 2 mL pressure vial which was then securely capped. The vial was heated at 150° C. for 20 hours. After cooling, the solid mass was dissolved in CH2Cl2 (25 mL) and extracted with saturated sodium carbonate (25 mL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was recrystallized from CH2Cl2 (5 mL) to afford the titled compound as a white solid (191 mg, 54%). 1H NMR (CDCl3) δ 1.54 (d, J=6.6 Hz, 3H), 3.54 (q, J=5.5 Hz, 2H), 3.94 (t, J=5.5 Hz, 2H), 4.59 (p, J=6.6 Hz, 1H), 5.05 (broad m, 1H), 5.08 (s, 1H), 5.34 (broad d,1H), 6.77 (m, 2H), 6.95 (t, J=9.1 Hz, 2H), 7.23 (m,1H), 7.32 (d, J=4.4 Hz, 4H), 8.09 (s, 1H), LC/MS (MH+) m/e 353.79 obs. was then securely capped After cooling extracted with saturated sodium carbonate (25 mL) The organic layer was dried over sodium sulfate concentrated under reduced pressure The residue was recrystallized from CH2Cl2 (5 mL)