Triethylamine → HCID 89689648, compound
Reaction equation
Br[C:2]1[N:3]=[C:4]([O:9][CH3:10])[C:5]([NH2:8])=[N:6][CH:7]=1.C(N(CC)CC)C.[C]=[O:19].CO.C1[CH2:26][O:25][CH2:24]C1>>[NH2:8][C:5]1[N:6]=[CH:7][C:2]([C:24]([O:25][CH3:26])=[O:19])=[N:3][C:4]=1[O:9][CH3:10]Participants
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 5-bromo-3-methoxypyrazin-2-amine (2.80 g, 13.7 mmol, 1 eq.; Jiang, B. et al. Bioorg. Med. Chem. (2001), 9, 1149-1154), [1,1,-Bis-(diphenylphosphino)ferrocen]palladium(II)-dichlorid (2.24 g, 2.75 mmol, 0.2 eq) and triethylamine (2.10 mL, 15.1 mmol, 1.1 eq) was placed in 600 mL autoclave and dissolved in 135 mL methanol/THF (10/1). The autoclave was flushed with carbon monoxide (3×) and was then pressurized with carbon monoxide to 9 bar. After 30 min at r.t. no conversion was obtained. The autoclave was again pressurized with carbon monoxide to 9 bar and subsequently heated to 100° C. In the course of the reaction, carbon monoxide consumption was observed (decrease of CO pressure). The autoclave was cooled to r.t., flushed with inert gas and the reaction mixture was filtered through a small pad of Celite. LC-MS analysis showed full conversion. The volatile components were removed in vacuo and the material observed this way (1.8 g, 62%) contained the title compound in 92% purity (UPLC-MS, area-%) and was used in the following without further purification.
Workup
- customThe autoclave was flushed with carbon monoxide (3×)
- customAfter 30 min at r.t. no conversion was obtained
- temperatureThe autoclave was cooled to r.t.
- customflushed with inert gas
- filtrationthe reaction mixture was filtered through a small pad of Celite
- customThe volatile components were removed in vacuo
- customfollowing without further purification
Sources & evidence
- ORD record
- ord-ae09c76ea42946239599241b61c0618c
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09260435B2
Reaction notes
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