Sodium Hydroxide → 5-Ethynylpyridin-2-amine

HRID 1293753Notes

Reaction equation

HRID 1293753 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-a8985305bddb4b8d8d083cc93125dc7a
Source dataset
uspto-grants-2007_07
Patent number
US07238808B2

Reaction notes

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