Tetrabutylammonium Fluoride → HCID 58456366, compound

HRID 410529Notes

Reaction equation

HRID 410529 reaction equation
[Si]([O:18][CH2:19][C:20]([C:23]1[S:24][C:25]([C:28]2[CH:29]=[C:30]([NH:34][C:35]3[N:40]=[C:39]([C:41]([F:44])([F:43])[F:42])[CH:38]=[CH:37][N:36]=3)[CH:31]=[CH:32][CH:33]=2)=[CH:26][N:27]=1)([CH3:22])[CH3:21])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH3:22][C:20]([C:23]1[S:24][C:25]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([NH:34][C:35]3[N:40]=[C:39]([C:41]([F:44])([F:42])[F:43])[CH:38]=[CH:37][N:36]=3)[CH:29]=2)=[CH:26][N:27]=1)([CH3:21])[CH2:19][OH:18]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67258164HCID 67258164, compound

Product 1

HCID 58456366HCID 58456366, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product of Step 4 (327 mg, 0.517 mmol) in THF (3 mL) was added TBAF (1.0 M, 1.55 mL, 1.55 mmol), and the mixture stirred at room temperature for 2 weeks at which point LCMS showed complete conversion. The mixture was concentrated in vacuo, then the residue purified by chromatography on silica gel (60:40 to 0:100, hexanes:ethyl acetate) to provide 162 mg (0.411 mmol, 79%) of 2-methyl-2-[5-(3-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]propan-1-ol as a white solid. MS APCI: [M+H]+ m/z 395.0. 1H NMR (400 MHz, CDCl3): δ 8.67 (d, J=4.9 Hz, 1H); 8.07 (s, 1H); 7.85 (s, 1H); 7.63 (s, 1H); 7.49 (d, J=8.2 Hz, 1H); 7.37 (t, J=7.9 Hz, 1H); 7.26 (d, J=7.7 Hz, 1H); 7.07 (d, J=4.9 Hz, 1H); 3.79 (s, 2H); 1.48 (s, 6H). rhSYK activity=+++

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue purified by chromatography on silica gel (60:40 to 0:100, hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-704291b8328e416e92d5f4fb3b2594d7
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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