(2S)-2-(Methylamino)propan-1-OL

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared by a procedure similar to that described for D27 starting from 2,4,6-trichloropyrimidine and (S)-2-(methylamino)propan-1-ol.

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2,4,6-trichloropyrimidine (5.42 mL, 47.1 mmol) and triethylamine (19.7 mL, 141 mmol) in acetonitrile (40 mL) was slowly added (S)-2-(methylamino)propan-1-ol (6.30 g, 70.7 mmol) in N,N-dimethylformamide (DMF) (3.00 mL) at 0° C. The reaction mixture was stirred at 0° C. for 1 h, filtered, dried over anhydrous Na2SO4, concentrated. Purification via flash chromatography column (petroleum ether/ethyl acetate=10/1) afforded the title product. at 0° C filtered dried over anhydrous Na2SO4 concentrated Purification via flash chromatography column (petroleum ether/ethyl acetate=10/1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The procedure described in Example 103, preparation of starting materials, was repeated using 5-fluoro-N-{3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}quinazolin-4-amine (obtained as described in Example 103, preparation of starting materials) and (2S)-2-(methylamino)propan-1-ol (obtained as described in Chacchio et al., Tetrahedron, 1995, 51, 5689) to give 5-{[(2S)-2-(methylamino)propyl]oxy}-N-{3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}quinazolin-4-amine in 71% yield; NMR Spectrum: (CDCl3) 1.30 (d, 3H), 2.28 (s, 3H), 2.52 (s, 3H), 2.53 (s, 3H), 3.20 (m, 1H), 4.09 (m, 1H), 4.21 (m, 1H), 6.89 (m, 2H), 7.14-7.07 (m, 2H), 7.45 (d, 1H), 7.63 (m, 2H), 8.26 (s, 1H), 8.63 (s, 1H); Mass spectrum: MH+ 430. The procedure described in Example 103, preparation of starting materials

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The procedure described in Example 3 (preparation of starting materials) was repeated using (2S)-2-(methylamino)propan-1-ol (obtained as described in Chacchio et al., Tetrahedron, 1995, 51, 5689) and 2-chloro-4-[(5-fluoroquinazolin-4-yl)amino]phenol (obtained as described in Example 4.5, preparation of starting materials) to give 2-chloro-4-[(5-{[(2S)-2-(methylamino)propyl]oxy}quinazolin-4-yl)amino]phenol in >100% yield; NMR spectrum (DMSO-d6) 1.20 (d, 3H), 2.40 (s, 3H), 3.20 (m, 1H), 4.15 (dd, 1H), 4.30 (dd, 1H), 7.00 (d, 1H), 7.10 (d, 1H), 7.30 (d, 1H), 7.60 (dd, 1H), 7.70 (t, 1H), 8.00 (d, 1H), 8.50 (s, 1H); Mass spectrum MH+ 359.4. The procedure described in Example 3 (preparation of starting materials)