4-Aminophenol → 4-(6-Fluoropyrimidin-4-yloxy)benzenamine

참여 물질

반응 단계

4-Amino-phenol (0.135 g, 1.21 mmol) is added in one portion to a suspension of NaH (60% free-flowing powder moistened with oil, 58.2 mg, 1.45 mmol, 1.2 equiv) in dioxane abs. (1.4 mL), under an argon atmosphere. When hydrogen evolution subsides, a solution of 4,6-difluoro-pyrimidine (0.141 g, 1.21 mmol) in dioxane (0.4 mL) Is added. The resulting dark mixture is stirred for 1.5 h at rt, quenched by addition of MeOH (2 mL) and concentrated in vacuo. After addition of CH2Cl2, the resulting suspension is filtered and concentrated in vacuo. The residue is purified by silica gel column chromatography (CH2Cl2/Et2O, 90/10, then 85/15) to afford the title compound as a white solid: ES-MS: 204.0 [M+H]+; single peak at tR=4.96 min (System 2); Rf=0.30 (CH2Cl2/Et2O, 85/15).

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