[NH2:1][C:2]1[N:7]=[C:6](Cl)[N:5]=[C:4]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:11]=2[F:17])[N:3]=1.C1N2CC[N:20](CC2)[CH2:19]1.C(#N)C>[C-]#N.C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[NH2:1][C:2]1[N:7]=[C:6]([C:19]#[N:20])[N:5]=[C:4]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:11]=2[F:17])[N:3]=1To 2-amino-4-chloro-6-(2,3-difluorophenylamino)-[1,3,5]triazine (Intermediate 55, 1.0 g, 3.89 mmol) was added DABCO (540 mg, 4.67 mmol), tetra n-butylammonium cyanide (1.15 g, 4.28 mmol) and anhydrous acetonitrile (15 mL). The reaction mixture was stirred at 50 C for 1 h, diluted with 50 mL ethyl acetate, extracted with 1M aq. citric acid (2×50 mL), water (2×50 mL), saturated brine (50 mL) and dried further over anhydrous sodium sulfate. Evaporation of the solvent gave a red gum which was purified by column chromatography on silica eluting with DCM-2% ethyl acetate to give the desired compound (429 mg, 69%). Method B HPLC-MS: MH+ requires m/z=249. Found: m/z=249, Rt=1.64 min (91%).
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