tert-Butanol → HCID 56603138, compound

HRID 1187715Notes

Reaction equation

HRID 1187715 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]=[C:19]([CH:22]=[CH:23][CH:24]=3)[C:20]#[N:21])[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:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11]2[N:16]=[C:15]([C:17]3[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=3)[C:20]([NH2:21])=[O:38])[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

Participants

4

Reactant 3

HCID 6386tert-ButanolHCID 522689Potassium Fluoride2×HCID 56603197HCID 56603197, compound

Product 1

HCID 56603138HCID 56603138, compound

Conditions

Temperature
80 °C

Procedure

192 mg of (S)-3-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}benzonitrile (Example 81) was added to 5 ml of t-butanol, and 384 mg of potassium fluoride supported on activated alumina was added thereto, and the mixture was stirred at 80° C. for 2 hours. 384 mg of potassium fluoride supported on activated alumina was added thereto, and the mixture was further stirred for 15 hours. The reaction solution was filtrated to remove precipitates, and then the filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 158 mg of the objective compound as white powder.

Workup

  1. additionwas added
  2. additionwas added
  3. stirringthe mixture was further stirred for 15 hours
  4. filtrationThe reaction solution was filtrated
  5. customto remove
  6. customprecipitates
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5fddddeb6af243618ddbcc3570ca3c6b
Source dataset
uspto-grants-2014_03
Patent number
US08673891B2

Reaction notes

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