Sodium Hydroxide → 4-Chloro-6-(1H-5-indolyloxy)-2-pyrimidinamine

Participants

Reaction Conditions

Reaction Steps

10 g (61 mMol) 2-amino-4,6-dichloro-pyrimidine and 8.1 g (61 mMol) 5-hydroxyindole are suspended in 250 ml acetone. Then 120 ml 1 N NaOH in water are added and the mixture is stirred at an oilbath temperature of 70° C. for 2 h. The reaction mixture is partially concentrated and the residue diluted with water. Extraction with 3 portions of EtOAc, washing the organic layers twice with water and brine, drying (Na2SO4), addition of 100 g SiO2 and concentration in vacuo gives a powder. This is put on top of a chromatography column (SiO2; EtOAc/hexane 3:7) and eluted with EtOAc/hexane 3:7. Crystallization from hexane gives the title compound: m.p.: 192° C.; MS: [M+1]+=261; HPLC: AtRet=12.4.

Provenance & Evidence