Tetrahydrofuran → 2-(4-Aminopyrimidin-2-yl)propan-2-ol
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4](C(OCC)=O)[N:3]=1.[CH3:13][Mg]Br.[O:16]1[CH2:20][CH2:19]CC1>>[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:20]([OH:16])([CH3:19])[CH3:13])[N:3]=1Participants
4
Conditions
- Temperature
- 0 °C
Procedure
To a solution of ethyl 4-aminopyrimidine-2-carboxylate (840 mg, 5.0 mmol) in anhydrous tetrahydrofuran (50 mL) cooled at −20° C. was added a solution of methylmagnesium bromide in THF (8.5 mL, 25.0 mmol, 3.0 M) over a period of 5 minutes. The reaction mixture was stirred at 0° C. for another 2 h. It was then quenched with saturated NH4Cl (20 mL) and concentrated under reduced pressure. The residue was extracted with ethyl acetate (5×40 mL). The combined organic layer was dried over anhydrous Mg2SO4, filtered, and evaporated under reduced pressure. The residue was purified by reverse-phase Combiflash to afford 264a as yellow solid (240 mg, 32%) MS-ESI: [M+H]+ 154.1
Workup
- customIt was then quenched with saturated NH4Cl (20 mL)
- concentrationconcentrated under reduced pressure
- extractionThe residue was extracted with ethyl acetate (5×40 mL)
- dry with materialThe combined organic layer was dried over anhydrous Mg2SO4
- filtrationfiltered
- customevaporated under reduced pressure
- customThe residue was purified by reverse-phase Combiflash
Sources & evidence
- ORD record
- ord-11752dcbef7f4ad9815de5fb0e3f2889
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09238655B2
Reaction notes
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