Ammonium Hydroxide → 6-(Trifluoromethyl)pyrimidin-4-amine

The procedure was derived from methods described in U.S. Pat. No. 5,756,275 and WO 02/38569. In a 250 mL round bottom flask, 6-trifluoromethyl-4-pyrimidinol (10 g, 60.9 mmol) was dissolved in 70 mL phosphorus oxychloride (0.73 mol). The solution was heated at reflux for 7 h. The cooled reaction solution was then added gradually to 200 mL 30% ammonium hydroxide, and the resulting mixture was stirred overnight at room temperature. The reaction mixture was extracted with ethyl acetate (2×100 mL), and the combined extracts were dried (MgSO4) and evaporated in vacuo to give 6-trifluoromethyl-pyrimidin-4-ylamine (1.4 g, yield 14%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 8.50 (s, 1 H), 7.60 (broad s, 2 H), 6.90 (s, 1 H); LC-MS m/z 164.1 [M+H]+.

1. temperatureThe solution was heated
2. temperatureat reflux for 7 h
3. customThe cooled reaction solution
4. extractionThe reaction mixture was extracted with ethyl acetate (2×100 mL)
5. dry with materialthe combined extracts were dried (MgSO4)
6. customevaporated in vacuo

ORD record

ord-1cc8650490ca42ee86bc975a0c1b6a9c

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08580798B2