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TBAF tetrahydrofuran → (S)-N2-[1-(4-fluorophenyl)ethyl]-6-(oxazol-5-yl)-N4-(pyrazin-2-yl)pyrimidine-2,4-diamine

HRID 1187687
Notes
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Reaction equation

HRID 1187687 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]([NH:17][C:18]3[CH:23]=[N:22][CH:21]=[CH:20][N:19]=3)[CH:14]=[C:13]([C:24]3[O:28][C:27]([Si](C(C)C)(C(C)C)C(C)C)=[N:26][CH:25]=3)[N:12]=2)[CH3:9])=[CH:4][CH:3]=1.O1CCCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11]2[N:16]=[C:15]([NH:17][C:18]3[CH:23]=[N:22][CH:21]=[CH:20][N:19]=3)[CH:14]=[C:13]([C:24]3[O:28][CH:27]=[N:26][CH:25]=3)[N:12]=2)[CH3:9])=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 11078149TBAF tetrahydrofuranHCID 86659385(S)-N2-[1-(4-fluorophenyl)ethyl]-N4-(pyrazin-2-yl)-6-[2-(triisopropylsilyl)oxazol-5-yl]pyrimidine-2,4-diamine

Product 1

HCID 56599390(S)-N2-[1-(4-fluorophenyl)ethyl]-6-(oxazol-5-yl)-N4-(pyrazin-2-yl)pyrimidine-2,4-diamineYield 69.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent
HCID 8857
Ethyl Acetate
Solvent

Procedure

122 mg of (S)—N2-[1-(4-fluorophenyl)ethyl]-N4-(pyrazin-2-yl)-6-[2-(triisopropylsilyl)oxazol-5-yl]pyrimidine-2,4-diamine was dissolved in 1.2 ml of tetrahydrofuran, and 0.5 ml of 1 M tetrabutylammonium fluoride tetrahydrofuran solution was added. The reaction solution was stirred at room temperature for 20 min, and then diluted with ethyl acetate. The solution was washed in turn with water and brine and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and then the obtained residue was purified by silica gel column chromatography to obtain 60 mg of (S)—N2-[1-(4-fluorophenyl)ethyl]-6-(oxazol-5-yl)-N4-(pyrazin-2-yl)pyrimidine-2,4-diamine as white powder. The obtained compound was subjected to hydrochlorination using a conventional method to obtain 45 mg of the objective compound as pale orange powder.

Workup

  1. washThe solution was washed in turn with water and brine
  2. dry with materialdried over magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-524a4789ad874731bd5e415214cf38f6
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08673891B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes