Tert-Butyl 6-((2-tert-butoxy-3-(5-methylpyridin-2-yl)cyclopropyl)methoxy)-2-methylpyrimidin-4-yl((5-methyl-1,3,4-thiadiazol-2-yl)methyl)carbamate → 6-((2-Tert-butoxy-3-(5-methylpyridin-2-yl)cyclopropyl)methoxy)-2-methyl-N-((5-methyl-1,3,4-thiadiazol-2-yl)methyl)pyrimidin-4-amine
Reaction equation
[C:1]([O:5][CH:6]1[CH:8]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][N:10]=2)[CH:7]1[CH2:16][O:17][C:18]1[N:23]=[C:22]([CH3:24])[N:21]=[C:20]([N:25]([CH2:33][C:34]2[S:35][C:36]([CH3:39])=[N:37][N:38]=2)C(=O)OC(C)(C)C)[CH:19]=1)([CH3:4])([CH3:3])[CH3:2]>C(O)(C(F)(F)F)=O>[C:1]([O:5][CH:6]1[CH:8]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][N:10]=2)[CH:7]1[CH2:16][O:17][C:18]1[N:23]=[C:22]([CH3:24])[N:21]=[C:20]([NH:25][CH2:33][C:34]2[S:35][C:36]([CH3:39])=[N:37][N:38]=2)[CH:19]=1)([CH3:4])([CH3:3])[CH3:2]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
The solution of 12-7 (41 mg, 0.074 mmol) in TFA (0.5 mL) was stirred for 1 h at rt. The excess TFA was removed under reduced pressure. The residue was dissolved in dichloromethane (10 mL) and adjusted to pH=9-10 with saturated NaHCO3 aqueous solution. The mixture was extracted with EtOAc, dried over sodium sulfate, concentrated under reduced pressure and purified by reverse phase column (Waters Sunfire Prep C18 OBD, 5-95% methanol in water with 0.1% NH3H2O modifier). The product was obtained as a white solid (22 mg, 65%). 1H NMR (500 MHz, CDCl3) δ 8.36 (s, 1H), 7.51 (s, 1H), 7.12 (d, J=4.8 Hz, 1H), 5.63 (s, 1H), 5.43 (s, 1H), 4.91 (d, J=6.3 Hz, 2H), 4.36 (d, J=6.8 Hz, 2H), 3.66 (s, 1H), 2.73 (s, 3H), 2.47 (s, 3H), 2.33 (m, 4H), 2.03 (m, 1H), 1.06 (s, 9H); LRMS (ES) calculated M+H for C23H31N6O2S: 455.6. Found:455.2.