Pyrazine → HCID 71292823, compound
Reaction equation
CC1(C)CCCC(C)(C)N1.C([Li])CCC.[N:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1.[CH3:22][O:23][C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[O:30][CH:29]([OH:34])[CH2:28][CH2:27]2>O1CCCC1.CCCCCC>[OH:34][CH:29]([C:17]1[CH:18]=[N:19][CH:20]=[CH:21][N:16]=1)[CH2:28][CH2:27][C:26]1[CH:25]=[C:24]([O:23][CH3:22])[CH:33]=[CH:32][C:31]=1[OH:30]Participants
Conditions
- Temperature
- 0 °C
Procedure
A solution of 2,2,6,6-tetramethyl-piperidine (8.5 ml, 50.4 mmol) in 200 ml of anhydrous tetrahydrofuran was cooled to −30° C., n-butyllithium (20 ml of a 2.5 M solution in hexane, 50 mmol) was added dropwise, and the mixture stirred for 30 min at 0° C. After cooling at −70° C., a solution of pyrazine (4.0 g, 49.9 mmol) in 50 ml of anhydrous tetrahydrofuran was added dropwise. After 10 min at −70° C., 6-methoxy-chroman-2-ol (1.8 g, 10.0 mmol) was added and stirring was continued at −70° C. for 1.5 h. The reaction mixture was quenched with 20 ml of water and hydrochloric acid added until pH 5-6 was reached. After extraction with ethyl acetate, the organic layer was washed with water and brine, dried with sodium sulfate and concentrated. The obtained crude orange oil (960 mg) was used without further purification.
Workup
- temperatureAfter cooling at −70° C.
- waitAfter 10 min at −70° C.
- stirringstirring
- waitwas continued at −70° C. for 1.5 h
- customThe reaction mixture was quenched with 20 ml of water and hydrochloric acid
- additionadded until pH 5-6
- extractionAfter extraction with ethyl acetate
- washthe organic layer was washed with water and brine
- dry with materialdried with sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-9d5556ccaa444958a5ed5410bd8e7410
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08912224B2
Reaction notes
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