Methyl iodide → HCID 58114942, compound

HRID 2197506Notes

Reaction equation

[C:1](=O)([O-])[O-].[K+].[K+].CI.[OH:9][C:10]1[C:11]([C:26]2[O:30][N:29]=[C:28]([C:31]([F:34])([F:33])[F:32])[CH:27]=2)=[C:12]([O:20][C:21](=[O:25])[CH:22]([CH3:24])[CH3:23])[C:13]2[C:14]([N:19]=1)=[N:15][CH:16]=[CH:17][N:18]=2>C(#N)C.C(OCC)(=O)C.O>[CH3:1][N:19]1[C:14]2=[N:15][CH:16]=[CH:17][N:18]=[C:13]2[C:12]([O:20][C:21](=[O:25])[CH:22]([CH3:24])[CH3:23])=[C:11]([C:26]2[O:30][N:29]=[C:28]([C:31]([F:33])([F:32])[F:34])[CH:27]=2)[C:10]1=[O:9]

Participants

Conditions

Temperature: 100 °C

Procedure

Potassium carbonate (0.023 g) and methyl iodide (0.01 ml) were added to isobutyric acid 6-hydroxy-7-(3-trifluoromethyl-isoxazol-5-yl)-pyrido[2,3-b]pyrazin-8-yl ester (Example 6.6) (0.030 g) in acetonitrile (1.5 ml). The reaction mixture was heated in a microwave to 100° C. for 10 minutes. The reaction mixture was diluted with ethyl acetate and water. The phases were separated. The organic phase was washed with water and brine, dried over magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane 1:2 to 1:1) to give Compound No. B8 of Table B (0.025 g) as a colourless oil that solidified on standing.

Workup

customThe phases were separated
washThe organic phase was washed with water and brine
dry with materialdried over magnesium sulfate
concentrationconcentrated
customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane 1:2 to 1:1)
customto give Compound No

Sources & evidence

ORD record: ord-6df65ecbcf124fc9aef86c1d7bf149c6
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338598B2

Reaction notes

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