Trimethyl orthoacetate → 3-Cyclohexyl-2-methyl-3H-imidazo[4,5-b]pyridin-5-ol
Reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([OH:15])=[N:6][C:7]=1[NH:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.[C:16](OC)(OC)(OC)[CH3:17]>C(O)(C(F)(F)F)=O>[CH:9]1([N:8]2[C:7]3=[N:6][C:5]([OH:15])=[CH:4][CH:3]=[C:2]3[N:1]=[C:16]2[CH3:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
5-Amino-6-(cyclohexylamino) pyridin-2-ol (0.1 g, 0.482 mmol) was dissolved in trimethyl orthoacetate (3.0 mL, 27.4 mmol). Several drops of TFA were added and the reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated and the residues were diluted with water/acetonitrile (1:1). The mixture was purified via HPLC to give the title compound (0.006 g). LCMS m/z=232.30 [M+H]+; 1H NMR (400 MHz, methanol-d4) δ ppm 1.43-1.5 (m, 1H), 1.53-1.63 (m, 2H), 1.83 (d, J=11.87 Hz, 1H), 2.01 (d, J=10.99 Hz, 4H), 2.64-2.74 (m, 2H), 2.89 (s, 3H), 4.51-4.57 (m, 1H), 6.90 (d, J=8.8 Hz, 1H), 8.0 (d, J=8.8 Hz, 1H).