Water → ((R)-1-[1,2,4]triazolo-[1,5-a]pyrimidin-7-ylpyrrolidin-2-yl)methyl methanesulfonate
Reaction equation
[N:1]1[N:5]2[C:6]([N:10]3[CH2:14][CH2:13][CH2:12][C@@H:11]3[CH2:15][OH:16])=[CH:7][CH:8]=[N:9][C:4]2=[N:3][CH:2]=1.C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26].O>ClCCl>[CH3:24][S:25]([O:16][CH2:15][C@H:11]1[CH2:12][CH2:13][CH2:14][N:10]1[C:6]1[N:5]2[N:1]=[CH:2][N:3]=[C:4]2[N:9]=[CH:8][CH:7]=1)(=[O:27])=[O:26]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
1.5 g of ((R)-1-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylpyrrolidin-2-yl)methanol are dissolved in 15 ml of dichloromethane with stirring, and 1.9 ml of triethylamine are added. This solution is cooled to 0° C., and a solution of 0.8 ml of methanesulfonyl chloride in 5 ml of dichloromethane is added dropwise. When the addition is complete, the mixture is allowed to warm to RT for 12 h. For workup, the solution is poured into equal proportions by volume of water, the organic phase is extracted to exhaustion with ethyl acetate, the combined organic phases are dried over sodium sulfate, filtered off with suction, evaporated and chromatographed on silica gel, giving 1.1 g of ((R)-1-[1,2,4]triazolo-[1,5-a]pyrimidin-7-ylpyrrolidin-2-yl)methyl methanesulfonate as colourless oil;
Workup
- additionWhen the addition
- temperatureto warm to RT for 12 h
- extractionthe organic phase is extracted to exhaustion with ethyl acetate
- dry with materialthe combined organic phases are dried over sodium sulfate
- filtrationfiltered off with suction
- customevaporated
- customchromatographed on silica gel
Sources & evidence
- ORD record
- ord-bee043620d24404dbe79aa22d6a6ffd2
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08546406B2
Reaction notes
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