Trimethylaluminum → HCID 20161352, compound

HRID 247041Notes

Reaction equation

HRID 247041 reaction equation
[CH2:1]([N:5]1[CH2:9][C:8]([NH:10][C:11]2[N:15]([CH2:16][CH2:17][C:18]#[C:19][CH3:20])[N:14]=[CH:13][C:12]=2[C:21]#[N:22])=[CH:7][C:6]1=[O:23])[CH2:2][CH2:3][CH3:4].C[Al](C)C>ClCCl.CCCCCCC>[NH2:22][C:21]1[C:7]2[C:6](=[O:23])[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:9][C:8]=2[N:10]=[C:11]2[N:15]([CH2:16][CH2:17][C:18]#[C:19][CH3:20])[N:14]=[CH:13][C:12]=12

Participants

5

Reactant 2

HCID 16682925TrimethylaluminumHCID 20161358HCID 20161358, compound

Product 1

HCID 20161352HCID 20161352, compoundYield 56.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8900HeptaneSolvent

Procedure

To a solution of 5-[N-(n-butyl)-2-oxo-3-pyrrolin-4-yl]amino-1-(pent-3-ynyl)-4-cyanopyrazole (0.88 g.) in dry dichloromethane (20 ml.) was added a solution of trimethylaluminium in heptane (4.2 ml. of a 1.35 M solution) while stirring at room temperature under nitrogen. After stirring overnight, the reaction was quenched by the cautious addition of 3N aqueous hydrochloric acid until gas evolution had ceased. The precipitated aluminium salts were solubilized by addition of a 10% w/v aqueous solution of sodium hydroxide and the product was extracted into EtOAc. The extract was washed with 10% w/v aqueous sodium hydroxide solution and then brine, dried (Na2SO4), and evaporated to leave a light yellow solid. Recrystallization from toluene/hexane gave the title compound as a white crystalline powder (0.5 g.): m.p. 171°-172.5°.

Workup

  1. customthe reaction was quenched by the cautious addition of 3N aqueous hydrochloric acid until gas evolution
  2. additionThe precipitated aluminium salts were solubilized by addition of a 10% w/v aqueous solution of sodium hydroxide
  3. extractionthe product was extracted into EtOAc
  4. washThe extract was washed with 10% w/v aqueous sodium hydroxide solution
  5. dry with materialbrine, dried (Na2SO4)
  6. customevaporated
  7. customto leave a light yellow solid
  8. customRecrystallization from toluene/hexane

Sources & evidence

ORD record
ord-4f9391568fb7469398cceafa1a212398
Source dataset
uspto-grants-1987_11
Patent number
US04705793

Reaction notes

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