4-Aminophenol → 2-Amino-5-(4-chlorophenoxy)-4-(4-hydroxyanilino)pyrimidine hydrochloride

Participants

Reaction Conditions

Reaction Steps

Nitrogen was bubbled through a suspension of 10.11 g (27.5 mmol) of 4-chloro-5-(4-chlorophenoxy)-2-(diisopropylaminomethyleneamino)pyrimidine (see Example 2) in 205 ml of methanol for 10 minutes. Then 3.18 g (29.1 mmol) of 4-aminophenol was added and nitrogen bubbled through the suspension for 5 minutes. The solution was then tightly sealed and stirred at 24° C. for 20 hours. Then 50 ml of concentrated hydrochloric acid was added to the mixture and refluxed for 140 minutes. The mixture was cooled and spin evaporated to one-half the original volume and then stored at 3° C. After 3 hours, a large precipitate had formed which was collected by filtration and washed quickly with cold methanol. The filter cake was suspended in 79 ml of CH2Cl2 and the suspension was boiled for 5 minutes. The solids were collected by filtration, washed with CH2Cl2 and dried in vacuo at 100° C. 8.6 g (86%) of product as a pale yellow powder was obtained, mp 288-289° C.

Provenance & Evidence