[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([NH:9][CH2:10][C:11]([CH3:14])([OH:13])[CH3:12])=[CH:4][N:3]=1.[O:15]1[CH:20]=[CH:19][CH2:18][CH2:17][CH2:16]1.O>ClCCl.CC1C=CC(S(O)(=O)=O)=CC=1.N1C=CC=CC=1>[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([NH:9][CH2:10][C:11]([CH3:14])([O:13][CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20][O:15]2)[CH3:12])=[CH:4][N:3]=1
To a mixture of 1-(2,4-dichloropyrimidin-5-ylamino)-2-methylpropan-2-ol (258 mg, 1.09 mmol) and 3,4-dihydro-2H-pyran (0.200 ml, 2.18 mmol) in dichloromethane (7 ml) was added pyridine 4-methylbenzenesulfonate (13.7 mg, 0.055 mmol) and the reaction mixture was stirred for 16 hours. The reaction mixture was poured into water and extracted with Et2O. The organic layers were dried over Na2SO4, filtered and concentrated in vacuo to give a crude oil. The crude residue was purified by silica gel chromatography (hexane/ethyl acetate, 100:0 to 3:1) to afford 2,4-dichloro-N-(2-methyl-2-(tetrahydro-2H-pyran-2-yloxy)propyl)pyrimidin-5-amine (315 mg, 0.982 mmol, 90% yield) as a pale yellow oil. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.18 (s, 3H) 1.23 (s, 3H) 1.25-1.75 (m, 6H) 3.27-3.32 (m, 2H) 3.37-3.49 (m, 1H) 3.69-3.83 (m, 1H) 4.74-4.86 (m, 1H) 5.75 (t, J=6.32 Hz, 1H) 8.36 (s, 1H).
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