Benzyl Bromide → HCID 178510968, compound

HRID 2109975Notes

Reaction equation

HRID 2109975 reaction equation
[OH:1][C:2]1[N:7]2[N:8]=[CH:9][C:10]([CH2:11][CH2:12][CH2:13][CH2:14][C:15]#[N:16])=[C:6]2[N:5]=[C:4]([SH:17])[N:3]=1.[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CCN(C(C)C)C(C)C>CN1CCCC1=O>[CH2:18]([S:17][C:4]1[N:3]=[C:2]([OH:1])[N:7]2[N:8]=[CH:9][C:10]([CH2:11][CH2:12][CH2:13][CH2:14][C:15]#[N:16])=[C:6]2[N:5]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 81531DiisopropylethylamineHCID 178510969HCID 178510969, compound

Product 1

HCID 178510968HCID 178510968, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of compound (3) (5.3 g, 21,3 mmol) in N-methylpyrrolidinone (30 mL) was degassed in vacuum for 5 min. Benzyl bromide (2.28 mL, 19. 1 mmol) and DIEA (4.4 mL, 25 mmol) were added and the reaction mixture was stirred at room temperature under vacuum for 30 min. Sol-vent was removed under reduced pressure and the residue was diluted with EtOAc. The acetate solution was washed with 1 M HCl followed by brine. Organic extract was dried over anhydrous Na2 SO4, filtered, and concentrated. The residue was triturated in a mixture solvent of hexane, ether and EtOAc, and filtered to give 5-(2-benzylsulfanyl-4-hydroxy-pyrazolo[1,5-a][1,3,5]triazin-8-yl)-pentanenitrile (4) as a solid (6.0 g. 93%).

Workup

  1. customSol-vent was removed under reduced pressure
  2. additionthe residue was diluted with EtOAc
  3. washThe acetate solution was washed with 1 M HCl
  4. extractionOrganic extract
  5. customwas dried over anhydrous Na2 SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was triturated in a mixture solvent of hexane, ether and EtOAc
  9. filtrationfiltered

Sources & evidence

ORD record
ord-ed67ecd06e004792adec3dd3b56bc4b5
Source dataset
uspto-grants-2009_04
Patent number
US07517882B2

Reaction notes

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