Triethylamine → 5-(Chloromethyl)-2-(methylthio)pyrimidine
Reaction equation
[CH3:1][S:2][C:3]1[N:8]=[CH:7][C:6]([CH2:9]O)=[CH:5][N:4]=1.C(N(CC)CC)C.CS([Cl:22])(=O)=O>ClCCl>[Cl:22][CH2:9][C:6]1[CH:5]=[N:4][C:3]([S:2][CH3:1])=[N:8][CH:7]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
To a cold solution of [2-(methylthio)pyrimidin-5-yl]methanol (0.7813 g, 5.0 mmol) in anhydrous dichloromethane (10 mL, 0° C.) was added triethylamine (0.836 mL, 8.2 mmol) followed by the addition of methanesulfonyl chloride (0.465 mL, 6.0 mmol). The reaction mixture stirred at 0° C. under a nitrogen atmosphere for 30 minutes then at room temperature for 3.5 hours. The reaction was quenched with sodium bicarbonate (5%, 100 mL)) and extracted with dichloromethane (50 mL). The organic extracts were concentrated and the residue was purified by flash chromatography (silica gel) using 15% ethyl acetate in hexane to afford the desired compound (0.720 g, 82%) as a white solid. 1H-NMR ((CD3OD, 400 MHz) δ 8.60 (s, 2H), 4.64 (s, 2H), 2.54 (s, 3H); ES-HRMS m/z 175.0106 (M+H C6H7N2ClS requires 175.0091).
Workup
- waitat room temperature for 3.5 hours
- customThe reaction was quenched with sodium bicarbonate (5%, 100 mL)) and
- extractionextracted with dichloromethane (50 mL)
- concentrationThe organic extracts were concentrated
- customthe residue was purified by flash chromatography (silica gel)
Sources & evidence
- ORD record
- ord-f9f7269bcdd24f69af2937eaa393ce2f
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07629363B2
Reaction notes
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