tert-Butanol → HCID 56837389, compound

HRID 1187706Notes

Reaction equation

HRID 1187706 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11]2[N:16]=[C:15]([C:17]3[CH:18]=[CH:19][C:20]([C:23]#[N:24])=[N:21][CH:22]=3)[CH:14]=[C:13]([NH:25][C:26]3[CH:31]=[N:30][CH:29]=[CH:28][N:27]=3)[N:12]=2)[CH3:9])=[CH:4][CH:3]=1.[F-].[K+].C([OH:38])(C)(C)C>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([NH:10][C:11]2[N:16]=[C:15]([C:17]3[CH:18]=[CH:19][C:20]([C:23]([NH2:24])=[O:38])=[N:21][CH:22]=3)[CH:14]=[C:13]([NH:25][C:26]3[CH:31]=[N:30][CH:29]=[CH:28][N:27]=3)[N:12]=2)[CH3:9])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 6386tert-ButanolHCID 522689Potassium FluorideHCID 56603078HCID 56603078, compound

Product 1

HCID 56837389HCID 56837389, compound

Conditions

Temperature
90 °C

Procedure

To 38 mg of (S)-5-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}picolinonitrile, was added t-butanol, and 60 mg of potassium fluoride supported on activated alumina was added thereto, and the mixture was stirred at 90° C. for 4 hours. The reaction solution was filtrated to remove precipitates, and then the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 25 mg of the objective compound as an amorphous solid.

Workup

  1. additionwas added
  2. filtrationThe reaction solution was filtrated
  3. customto remove
  4. customprecipitates
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7318c6f4c27842eea421dcab4f838bf0
Source dataset
uspto-grants-2014_03
Patent number
US08673891B2

Reaction notes

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