4,6-Dichloropyrimidine → Methyl 3-(6-chloropyrimidin-4-ylamino)benzoate
Reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[NH2:9][C:10]1[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=1)[C:13]([O:15][CH3:16])=[O:14].CCN(C(C)C)C(C)C>C(O)CCC>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:9][C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=2)[C:13]([O:15][CH3:16])=[O:14])[CH:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 110 °C
Procedure
To a stirred solution of 4,6-dichloropyrimidine (0.5 g, 3.7 mmol) in n-butanol (10 mL) was added methyl 3-aminobenzoate (0.498 g, 3.7 mmol) and DIPEA (0.65 g, 5.0 mmol) and the reaction mixture was heated at 110° C. for 12 h. It was cooled and excess n-butanol was removed under reduced pressure. The residue was extracted with EtOAc (2×30 mL) and the combined EtOAc extract was washed with water (5 mL), brine (2.5 mL), dried over Na2SO4 and concentrated under reduced pressure. The residue was stirred with pet ether (30 mL) for 30 min, the pet ether removed by decantation and the solid obtained was dried under high vacuum to give methyl 3-(6-chloropyrimidin-4-ylamino)benzoate (0.3 g, 34%) as light brown solid.
Workup
- temperatureIt was cooled
- customexcess n-butanol was removed under reduced pressure
- extractionThe residue was extracted with EtOAc (2×30 mL)
- extractionthe combined EtOAc extract
- washwas washed with water (5 mL), brine (2.5 mL)
- dry with materialdried over Na2SO4
- concentrationconcentrated under reduced pressure
- customthe pet ether removed by decantation
- customthe solid obtained
- customwas dried under high vacuum
Sources & evidence
- ORD record
- ord-254b1541220b4bb5a4410ce218704bb8
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08445498B2
Reaction notes
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