Tetrabutylammonium Fluoride → 2-tert-Butyl-6-ethynyl-pyrazolo[1,5-a]pyrimidine

HRID 2042157Notes

Reaction equation

HRID 2042157 reaction equation
[C:1]([C:5]1[CH:19]=[C:8]2[N:9]=[CH:10][C:11]([C:13]#[C:14][Si](C)(C)C)=[CH:12][N:7]2[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>ClCCl>[C:1]([C:5]1[CH:19]=[C:8]2[N:9]=[CH:10][C:11]([C:13]#[CH:14])=[CH:12][N:7]2[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 583167152-tert-Butyl-6-trimethylsilanylethynyl-pyrazolo[1,5-a]pyrimidine

Product 1

HCID 583167022-tert-Butyl-6-ethynyl-pyrazolo[1,5-a]pyrimidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-tert-Butyl-6-trimethylsilanylethynyl-pyrazolo[1,5-a]pyrimidine (example 21, step 1) (2.4 g, 8.85 mmol) was dissolved in dichloromethane (10 ml) and tetrabutylammoniumfluoride on silica gel (7.1 g, 10.6 mmol, 1.5 mmol/g) was added at room temperature. The mixture was stirred for 2 hours at room temperature and purified by flash chromatography by directly loading the mixture onto a 70 g silica gel column and eluting with heptane:ethyl acetate 100:0->40:60. The desired compound was obtained as a light yellow solid (1.45 g, 83% yield), MS: m/e=200.2 (M+H+).

Workup

  1. custompurified by flash chromatography by directly loading the mixture onto a 70 g silica gel column
  2. washeluting with heptane:ethyl acetate 100:0->40:60

Sources & evidence

ORD record
ord-938352b79ebc4182b82cb696bab85ceb
Source dataset
uspto-grants-2013_11
Patent number
US08586581B2

Reaction notes

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