Phenol → 6-Phenoxypyrimidin-4-amine
Reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.[Na].[C:10]1([OH:16])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[OH-].[Na+]>>[O:16]([C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1Participants
5
Conditions
- Temperature
- 140 °C
Procedure
6-Chloropyrimidin-4-amine (3.00 g, 23.14 mmol) was added to a solution of sodium (0.197 g, 8.57 mmol) in phenol (11.29 g, 120 mmol) at 55° C. The mixture was heated at 140° C. for 2 h, then held at room temperature for 20 h. The reaction mixture was poured into 32% aqueous NaOH on ice/water keeping the mixture temperature below 20° C. The mixture was extracted with chloroform and the organic extract dried over calcium chloride and concentrated. The residue was purified by silica gel chromatography (2-20% ethyl acetate in hexanes) to afford 6-phenoxypyrimidin-4-amine (0.6 g, 3.21 mmol, 75% yield) as a white solid. LCMS R.T.=1.37; [M+H]+=197.95.
Workup
- extractionThe mixture was extracted with chloroform
- extractionthe organic extract
- dry with materialdried over calcium chloride
- concentrationconcentrated
- customThe residue was purified by silica gel chromatography (2-20% ethyl acetate in hexanes)
Sources & evidence
- ORD record
- ord-7243766aa3904fa2a14eba68f70d8a1c
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08309577B2
Reaction notes
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