N#N.[CH2:3]([O:10][C:11]1[C:12]([O:17][CH2:18][CH2:19][N:20]([CH3:22])[CH3:21])=[N:13][CH:14]=[CH:15][CH:16]=1)[C:4]1C=CC=CC=1.[NH4+].C(=O)([O-])[O-:25].[K+].[K+].C1(=O)OCCO1>CO.[Pd]>[CH3:22][N:20]([CH3:21])[CH2:19][CH2:18][O:17][C:12]1[C:11]([O:10][CH2:3][CH2:4][OH:25])=[CH:16][CH:15]=[CH:14][N:13]=1
To a N2-flushed solution of 2-{[3-(benzyloxy)pyridin-2-yl]oxy}-N,N-dimethylethanamine (from Step 2; 8.4 g, 31.1 mmol) in MeOH (100 mL) was added 10% Pd/C (0.8 g) followed by ammonium fornate (6.3 g, 100 mmol). The mixture was stirred at 50° C. under an atmosphere of nitrogen for 2 h. The reaction was filtered through Celite® and the solvent was removed under reduced pressure to yield a semi-crystalline material that was used without further purification in the next synthetic step. The crude product was dissolved in dry DMF (50 mL), potassium carbonate (6.0 g, 43 mmol) was added and the mixture was heated at 150° C. for 20 minutes. Ethylene carbonate (4.1 g, 46 mmol) was added and the heating was continued for another 1.5 h. Solids were filtered off and the filtrate was concentrated under reduced pressure. The residue was chromatographed on a column of silica using CHCl3/MeOH/NH4OH (95:5:0.2) as eluent to give 3.28 g (31%) of the title product as a light brown oil. HRMS m/z calcd for C11H18N2O3 (M)+ 226.1317. found 226.1323.
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