Methyl iodide → HCID 58114942, compound

HRID 241777Notes

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-9e2d210b30fe4ab3a8c557747beed1de
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653078B2

Reaction notes

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