4-Aminophenol → HCID 131733315, compound

Temperature

150 °C

4-Aminophenol (8.8 g, 80.6 mmol) and triethylamine (18.6 mL, 133.4 mmol) are added to a solution of 2,4-dichloropyrimidine (10.0 g, 67.1 mmol) in ethanol (150 mL). The reaction mixture is heated at 150° C. for 14 hours in a sealed flask. The batch is then cooled to ambient temperature and the solvent is evaporated off in vacuo. Dichloromethane (200 mL) is added to the residue, and then imidazole (9.1 g, 133.7 mmol) and tert-butyl(dimethyl)silyl chloride (12.1 g, 80.3 mmol) are added. The mixture is stirred for 15 hours at ambient temperature. The reaction mixture is diluted with water (200 mL). The phases are separated and the organic phase is washed with brine (1×100 mL). It is then dried over MgSO4, filtered and concentrated in vacuo. The residue is purified by chromatography over silica gel using ethyl acetate and heptane as eluants to obtain a solid. The latter is triturated in heptane, filtered off and rinsed with heptane to yield the expected compound in the form of a solid.

1. temperatureThe batch is then cooled to ambient temperature
2. customthe solvent is evaporated off in vacuo
3. additionDichloromethane (200 mL) is added to the residue
4. customThe phases are separated
5. washthe organic phase is washed with brine (1×100 mL)
6. dry with materialIt is then dried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe residue is purified by chromatography over silica gel
10. customto obtain a solid
11. customThe latter is triturated in heptane
12. filtrationfiltered off
13. washrinsed with heptane

ORD record

ord-2d0aa2217fe643688e44b896315e418b

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09108983B2