Diethyl Ether → 5-Ethynyl-2-methoxypyrimidine
Reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]#[C:10][Si](C)(C)C)=[CH:5][N:4]=1.[F-].[K+].C(OCC)C>CN(C=O)C.O>[C:9]([C:6]1[CH:5]=[N:4][C:3]([O:2][CH3:1])=[N:8][CH:7]=1)#[CH:10]Participants
6
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 2-methoxy-5-((trimethylsilyl)ethynyl)pyrimidine (520 mg, 2.5 mmol) in DMF (10 mL) and water (1 mL) was added potassium fluoride (290 mg, 5 mmol) and the mixture was stirred at 0° C. for 1 h. Diethyl ether (100 mL) was added and the solution was washed with water (2×10 mL) and brine (10 mL), dried over MgSO4 and concentrated. The title compound was isolated by silica gel:chromatography (9:1 CH2Cl2/hexane) as a clear oil (120 mg, 36%). 1H NMR (400 MHz, CDCl3) δ 8.62 (s, 2H), 4.05 (s, 3H), 3.28 (s, 1H).
Workup
- washthe solution was washed with water (2×10 mL) and brine (10 mL)
- dry with materialdried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-52fa1ea3183c4df9b1e94989a1e9d9c0
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08410150B2
Reaction notes
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