[CH3:1][C:2]1[N:3]([C:8]2[N:13]=[C:12]([CH3:14])[C:11](Br)=[C:10]([CH3:16])[N:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.[OH-:17].[K+].O>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:1][C:2]1[N:3]([C:8]2[N:13]=[C:12]([CH3:14])[C:11]([OH:17])=[C:10]([CH3:16])[N:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1To a stirred solution containing 2.00 g (7.14 mmol) of 2-(2,5-dimethyl-1H-pyrrol-1-yl)-5-bromo-4,6-dimethylpyrimidine (4) in 16 mL of dioxane-degassed water 1:1 were added 132 mg (0.14 mmol) of Pd2dba3 followed by 242 mg (0.58 mmol) of 2-Di-tert-butylphosphino-2′,4′,6′-triisopropylbyphenyl (L1) and 1.2 g (21.42 mmol) of potassium hydroxide. The reaction mixture was stirred at 100° C. under argon atmosphere during 3 h. The reaction mixture was poured into 100 mL of water and extracted with two portions of 75 mL of ethyl acetate. The aqueous layer was acidified with HCl (pH 2-3) and then extracted with two portions of 100 mL of ethyl acetate. The combined organic solution was washed with a portion of 100 mL of brine, dried (MgSO4) and the concentrated under diminished pressure to afford the expected product as a light yellow crystals: yield 1.62 g (100%). 1H-NMR (CDCl3) δ 5.76 (s, 2H), 2.47 (s, 6H), 2.20 (s, 6H); 13C-NMR (CDCL3) δ 154.15, 149.87, 145.13, 128.74, 107.32, 18.40, 13.50.
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