Tetrabutylammonium Fluoride → HCID 67256425, compound

HRID 1845873Notes

Reaction equation

HRID 1845873 reaction equation
[Si]([O:8][CH2:9][CH:10]([C:20]1[CH:25]=[CH:24][N:23]=[C:22]([NH2:26])[N:21]=1)[O:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[Cl:19])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[NH2:26][C:22]1[N:21]=[C:20]([CH:10]([O:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=2[Cl:19])[CH2:9][OH:8])[CH:25]=[CH:24][N:23]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67257649HCID 67257649, compound

Product 1

HCID 67256425HCID 67256425, compoundYield 58.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(2-(tert-butyldimethylsilyloxy)-1-(2-chloro-4-fluorophenoxy)ethyl)pyrimidin-2-amine (20a) (830 mg) in tetrahydrofuran (15 mL) was added tetrabutyl-ammonium fluoride (1 g) and the mixture was stirred at room temperature for 5 days. The mixture was concentrated and purified by column chromatography using 0 to 10% methanol in dichloromethane to give the title compound (348 mg) as a white solid.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by column chromatography

Sources & evidence

ORD record
ord-d42a8d978d0a446e8f49e2673d8d2f0a
Source dataset
uspto-grants-2015_02
Patent number
US08952001B2

Reaction notes

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