Isopropanol → 1-((2-Chloro-5-fluoropyrimidin-4-ylamino)methyl)cyclohexanol
Reaction equation
Cl.[NH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH:5]1O.[Cl:11][C:12]1[N:17]=[C:16](Cl)[C:15]([F:19])=[CH:14][N:13]=1.CCN(C(C)C)C(C)C.C([OH:32])(C)C>>[Cl:11][C:12]1[N:17]=[C:16]([NH:2][CH2:3][C:4]2([OH:32])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]2)[C:15]([F:19])=[CH:14][N:13]=1Participants
5
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 2-(aminomethyl)cyclohexanol hydrochloride (0.09 g, 0.54 mmol) and 2,4-dichloro-5-fluoro-pyrimidine (0.10 g, 0.60 mmol) in isopropanol (2 mL) was added iPr2NEt (0.21 mL, 1.20 mmol). The reaction mixture was heated at 80° C. for 12 hours. The reaction mixture was concentrated under reduced pressure and the resulting residue was purified by silica gel chromatography (25%-75% EtOAc/hexanes) to afford desired product, 14a.
Workup
- concentrationThe reaction mixture was concentrated under reduced pressure
- customthe resulting residue was purified by silica gel chromatography (25%-75% EtOAc/hexanes)
Sources & evidence
- ORD record
- ord-b8b9de24efb5418aaaa7647138f7691f
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08829007B2
Reaction notes
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