Triethylamine → 4-(1H-5-indolyloxy)-2-pyrimidinamine

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][CH:13]=[CH:12]3)[CH:5]=[C:4](Cl)[N:3]=1.CCN(CC)CC>C1COCC1.[Pd]>[NH2:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][CH:13]=[CH:12]3)[CH:5]=[CH:4][N:3]=1

Participants

Procedure

A solution of 1.00 g (3.84 mMol) 5-(2-amino-6-chloro-pyrimidin-4-yloxy)-1H-indole (Step 24.1) and 562 μl (4.0 mMol) Et3N in 170 ml THF is hydrogenated in the presence of 0.7 g Pd/C (10%; Engelhard 4505). The catalyst is filtered off, the filtrate concentrated and the residue dissolved in EtOAc and H2O. The aqueous layer is extracted twice with water. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated. Column chromatography (SiO2; EtOAc/hexane 4:1) gives the title compound: MS: [M+1]+=227; TLC(EtOAc/hexane 4:1): Rf=0.4; HPLC: AtRet=8.5.