Triethylamine → 5-Chloro-pyrazine-2-carboxylic acid 2-(tetrahydro-pyran-2-yloxy)-ethyl ester
Reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1.[O:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[O:17][CH2:18][CH2:19]O.C(N(CC)CC)C.O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1>C(Cl)Cl>[O:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[O:17][CH2:18][CH2:19][O:9][C:8]([C:5]1[CH:4]=[N:3][C:2]([Cl:1])=[CH:7][N:6]=1)=[O:10]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of 5-chloro-pyrazine-2-carboxylic acid (prepared as in Example 29, 3.15 g, 19.94 mmol) in methylene chloride (50 mL) was treated with 2-(tetrahydropyran-2-yloxy)ethanol (2.91 g, 19.94 mmol). The solution was cooled to 0° C. and then was treated with triethylamine (5.60 mL, 39.88 mmol) and bis(2-oxo-3-oxazolidinyl)phosphinic chloride (5.07 g, 19.94 mmol). The mixture was stirred at 0° C. for 15 min and then at 25° C. for 24 h. The mixture was extracted with methylene chloride and water. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230–400 mesh, 2/1 hexanes/ethyl acetate) afforded 5-chloro-pyrazine-2-carboxylic acid 2-(tetrahydro-pyran-2-yloxy)-ethyl ester as a colorless oil (3.41 g, 60%).
Workup
- waitat 25° C. for 24 h
- extractionThe mixture was extracted with methylene chloride and water
- washThe organic layer was washed with a saturated aqueous sodium chloride solution
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-cbd182211b9344e29fe25a0807304221
- Source dataset
- uspto-grants-2006_11
- Patent number
- US07132425B2
Reaction notes
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