Reaction SMILES: [CH2:1]([N:3]([CH2:6][C:7]1[N:16]([CH3:17])[C:15](=[O:18])[C:14]2[C:9](=[CH:10][C:11]([Cl:37])=[C:12]([CH2:19][N:20]([C:24]3[CH:36]=[CH:35][C:27]([C:28](OC(C)(C)C)=[O:29])=[CH:26][CH:25]=3)[CH2:21][C:22]#[CH:23])[CH:13]=2)[N:8]=1)[CH2:4][CH3:5])[CH3:2].[NH2:38][CH2:39][C:40]1[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>ClCCl.FC(F)(F)C(O)=O.CN(C=O)C>[CH2:1]([N:3]([CH2:6][C:7]1[N:16]([CH3:17])[C:15](=[O:18])[C:14]2[C:9](=[CH:10][C:11]([Cl:37])=[C:12]([CH2:19][N:20]([C:24]3[CH:25]=[CH:26][C:27]([C:28]([NH:38][CH2:39][C:40]4[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=4)=[O:29])=[CH:35][CH:36]=3)[CH2:21][C:22]#[CH:23])[CH:13]=2)[N:8]=1)[CH2:4][CH3:5])[CH3:2]
Reactant: C#CCN(Cc1cc2c(=O)n(C)c(CN(CC)CC)nc2cc1Cl)c1ccc(C(=O)OC(C)(C)C)cc1
Reactant: NCc1cccnc1
Agent: F[P-](F)(F)(F)(F)F
Agent: c1ccc2c(c1)nnn2O[P+](N1CCCC1)(N1CCCC1)N1CCCC1
Solvent: CN(C)C=O
Solvent: O=C(O)C(F)(F)F
Solvent: ClCCl
Product: C#CCN(Cc1cc2c(=O)n(C)c(CN(CC)CC)nc2cc1Cl)c1ccc(C(=O)NCc2cccnc2)cc1
Reaction time: 0.92 h

Procedure:
A solution of tert-butyl 4-[N-[2-diethylaminomethyl-7-chloro-3-methyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate (Preparation Example 15) (0.090 g, 0.17 mmol) in dichloromethane (1.2 ml) and trifluoroacetic acid (1.6 ml) was stirred at. room temperature for 55 min with protection from the light. The solvents were then removed in vacuo and the oily residue was treated with dicloromethane/toluene, then concentrated in vacuo and the solid was dried in vacuo over P2O5. This solid was dissolved in anhydrous DMF (1.3 ml) and the solution was placed in an ice-bath under argon. A solution of 3-(aminomethyl)pyridine (0.028 g, 0.255 mmol) in anhydrous DMF (0.2 ml) was added followed by PyBOP® (0.093 g, 0.178 mmol) and finally diisopropylethylamine (0.131 g, 1.02 mmol). Stirring was continued at 0° C. for 3 min; then the ice-bath was removed and stirring was continued for an additional 3 h. The reaction mixture was partitioned between ethyl acetate (200 ml) and saturated aqueous sodium bicarbonate (100 ml). The organic layer was washed with more saturated aqueous sodium bicarbonate (100 ml) and brine (100 ml), dried (Na2SO4) and concentrated in vacuo. Purification by column chromatography, on elution with a gradient of methanolin dichloromethane (2 to 3%), afforded a glass which was reprecipitated from dichloromethane/hexanes. The white solid was collected by filtration, washed with hexanes and dried in vacuo over P2O5 (0.049 g, 52%), mp 180-182° C.; 1H-NMR (DMSO-d6) 0.95 (t, J=7.11 Hz, 6H, 2×CH2CH3), 2.58 (obscured, J=7.0 Hz, 4H, 2×CH2CH3), 3.19 (s, 1H, C≡CH), 3.62 (s, 3H, N3-Me), 3.70 (s, 2H, 2-CH2), 4.37 (s, 2H, CH2C≡C), 4.44 (d, J=5.7 Hz, 2H, CONHCH2), 4.77 (s, 2H, 6-CH2), 6.78 (d, J=8.9 Hz, 2H, 3,5′-ArH), 7.32 (dd, J=4.8, 7.8 Hz, 1H, pyr 5-H), 7.67 (d, J=7.7 Hz, 1H, pyr 4-H), 7.75 (d, J=8.7 Hz, 2H, 2′,6′-ArH), 7.80, 7.91 (2×s, 2H, 5-H, 8-H), 8.42 (d, J=5.3 Hz, pyr 6-H), 8.51 (s, 1H, pyr 2-H), 8.74 (t, J=6.03 Hz, 1H, CONH).; MS (ESI, m/z) 557,559 [(M+H)+, 100%, 38% respectively; Cl isotopic pattern]. FAB-HRMS; measured 557.2414; calculated for C31H34ClN6O2 (M+H)+: 557.2432.