[CH3:1][C:2]1[N:12]=[CH:11][C:5]2[N:6]=[CH:7][NH:8][C:9](=O)[C:4]=2[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)Cl.[C:37]([C:39]1[CH:40]=[C:41]([CH:43]=[CH:44][C:45]=1[F:46])[NH2:42])#[CH:38]>ClCCCl>[C:37]([C:39]1[CH:40]=[C:41]([NH:42][C:9]2[C:4]3[CH:3]=[C:2]([CH3:1])[N:12]=[CH:11][C:5]=3[N:6]=[CH:7][N:8]=2)[CH:43]=[CH:44][C:45]=1[F:46])#[CH:38]6Methyl-pyrido[3,4-d]pyrimid-4-one (44 mg, 0.27 mmol), polymer -supported triphenylphosphine (0.462 g of about 3.0 mmol P/g resin, 1.55 mmol) and anhydrous carbon tetrachloride (0.261 mL, 2.71 mmol) were combined in 1,2-dichloroethane (1.25 mL). The reaction mixture was heated to 60° C. under an atmosphere of dry nitrogen for 2 hours. 3-Ethynyl-4-fluoro-aniline (55 mg, 0.407 mmol) was added and heating was continued at 60° C. for 6 hours. The polymer was filtered off and washed several times with 50% methanol/chloroform. The filtrate and washings were concentrated in vacuo and flash chromatographed on silica with gradient from 0 to 10% methanol/methylene chloride to afford the title product (10 mg; M.P. 225° C.; LC-MS: 279 (MH+); anal. RP-HPLC: 3.94 min.).
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