Trifluoroacetic acid → 5-(2-(2-methoxypropan-2-yl)-7-morpholinothiazolo[5,4-d]pyrimidin-5-yl)-N-methylpyridin-2-amine

Reaction equation

Cl[C:2]1[N:3]=[C:4]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[C:5]2[N:10]=[C:9]([C:11]([O:14][CH3:15])([CH3:13])[CH3:12])[S:8][C:6]=2[N:7]=1.[CH3:22][N:23]([C:31]1[CH:36]=[CH:35][C:34](B2OC(C)(C)C(C)(C)O2)=[CH:33][N:32]=1)C(=O)OC(C)(C)C.C(O)(C(F)(F)F)=O>>[CH3:15][O:14][C:11]([C:9]1[S:8][C:6]2[N:7]=[C:2]([C:34]3[CH:35]=[CH:36][C:31]([NH:23][CH3:22])=[N:32][CH:33]=3)[N:3]=[C:4]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[C:5]=2[N:10]=1)([CH3:13])[CH3:12]

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 445416766-(Boc-methylamino)pyridine-3-boronic acid pinacol ester

HCID 866300674-(5-Chloro-2-(2-methoxypropan-2-yl)thiazolo[5,4-d]pyrimidin-7-yl)morpholine

Product 1

HCID 252538365-(2-(2-methoxypropan-2-yl)-7-morpholinothiazolo[5,4-d]pyrimidin-5-yl)-N-methylpyridin-2-amine

Procedure

Crude 4-(5-chloro-2-(2-methoxypropan-2-yl)thiazolo[5,4-d]pyrimidin-7-yl)morpholine (60 mg) was reacted with tert-butyl methyl(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)carbamate via general procedure A. This crude product was then treated with TFA to remove residual protecting group and purified via reverse phase HPLC to get 58.4 mg 102. MS (Q1) 401.2 (M)+.