Tetrabutylammonium Fluoride → HCID 66937323, compound

HRID 240591Notes

Reaction equation

HRID 240591 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[N:19]1[CH:20]=[N:21][N:22]2[CH:27]=[CH:26][C:25]([O:28][C:29]3[CH:34]=[CH:33][C:32]([NH:35][C:36]4[C:45]5[C:40](=[CH:41][CH:42]=[C:43]([NH:46][C:47]6[O:48][CH2:49][C:50]([CH2:53][O:54][Si](C(C)(C)C)(C7C=CC=CC=7)C7C=CC=CC=7)([CH3:52])[N:51]=6)[CH:44]=5)[N:39]=[CH:38][N:37]=4)=[CH:31][C:30]=3[CH3:72])=[CH:24][C:23]=12>C1COCC1>[N:19]1[CH:20]=[N:21][N:22]2[CH:27]=[CH:26][C:25]([O:28][C:29]3[CH:34]=[CH:33][C:32]([NH:35][C:36]4[C:45]5[C:40](=[CH:41][CH:42]=[C:43]([NH:46][C:47]6[O:48][CH2:49][C:50]([CH2:53][OH:54])([CH3:52])[N:51]=6)[CH:44]=5)[N:39]=[CH:38][N:37]=4)=[CH:31][C:30]=3[CH3:72])=[CH:24][C:23]=12

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66937217HCID 66937217, compound

Product 1

HCID 66937323HCID 66937323, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBAF (7.799 mmol, 7.79 mL, 1M in THF) was added to a solution of N4-(4-([1,2,4]triazolo[1,5-a]pyridin-7-yloxy)-3-methylphenyl)-N6-(4-((tert-butyldiphenylsilyloxy)methyl)-4-methyl-4,5-dihydrooxazol-2-yl)quinazoline-4,6-diamine (2.866 g, 3.900 mmol) in THF (60 mL). The reaction was stirred for 3 hours and then concentrated. The residue was purified by flash chromatography, eluting with EtOAc/Hex/MeOH 9:1:1 with 0.1% H2O to provide the title compound. MS APCI (+) m/z 497.4 (M+1) detected.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by flash chromatography
  3. washeluting with EtOAc/Hex/MeOH 9:1:1 with 0.1% H2O

Sources & evidence

ORD record
ord-9006c3a435304a7fb98630937f6ec9b4
Source dataset
uspto-grants-2014_02
Patent number
US08648087B2

Reaction notes

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