Sodium Hydroxide → 5-Ethynylpyridin-2-amine

HRID 558644Notes

Reaction equation

HRID 558644 reaction equation
FC(F)(F)C1[N:8]2N=CC=[C:7]2[N:6]=[C:5]([C:12]2[CH:17]=[CH:16]C(C(F)(F)F)=[CH:14][CH:13]=2)C=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[C:17]([C:12]1[CH:13]=[CH:14][C:7]([NH2:8])=[N:6][CH:5]=1)#[CH:16]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 715397317-(Trifluoromethyl)-5-(4-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyrimidine

Product 1

HCID 219548275-Ethynylpyridin-2-amineYield 36.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4-(6-amino-pyridin-3-yl)-2-methyl-but-3-yn-2-ol (example D.1 method 2 step 1) (22.5 g, 128 mmol) in toluene (500 mL) was refluxed in the presence of powdered NaOH (3.83 g, 96 mmol) for 16 h. The solvent was removed under reduced pressure to leave a brown residue which was purified by silica gel column chromatography with dichloromethane and ether, followed by trituration with heptane to give the title compound (5.5 g, 36%) (31.1 g, 100%) as light red solid. MS (EI) 118.1 [(M)+]; mp 143° C.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customto leave a brown residue which
  3. customwas purified by silica gel column chromatography with dichloromethane and ether

Sources & evidence

ORD record
ord-f74fb5a3a3db47e19a5d10d7082cc796
Source dataset
uspto-grants-2011_11
Patent number
US08063048B2

Reaction notes

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