Water → HCID 18789136, compound

HRID 1106524Notes

Reaction equation

HRID 1106524 reaction equation
Cl[C:2]1[N:7]2[N:8]=[CH:9][C:10]([N+:11]([O-:13])=[O:12])=[C:6]2[N:5]=[C:4]([CH3:14])[C:3]=1[CH2:15][CH2:16]Cl.[C:18]([NH2:22])([CH3:21])([CH3:20])[CH3:19].C(N(CC)CC)C.O>CN(C)C=O>[C:18]([N:22]1[C:2]2[N:7]3[N:8]=[CH:9][C:10]([N+:11]([O-:13])=[O:12])=[C:6]3[N:5]=[C:4]([CH3:14])[C:3]=2[CH2:15][CH2:16]1)([CH3:21])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 18789072HCID 18789072, compound

Product 1

HCID 18789136HCID 18789136, compoundYield 44.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 18 ml of anhydrous dimethylformamide were dissolved 1.75 g (6.36 mmol) of 7-chloro-6-(2-chloroethyl)-5-methyl-3-nitropyrazolo[1,5-a]pyrimidine, and 0.93 g (12.72 mmol) of tert-butylamine and 1.61 g (15.94 mmol) of triethylamine were successively added to the solution, and the mixture was stirred at room temperature for 6 hours. Thereafter, the reaction mixture was poured into water and extracted with ethyl acetate (150 ml×2). The ethyl acetate layers were put together, washed with a saturated saline solution and dried over anhydrous magnesium sulfate, and the solvent was then distilled off. The residue was subjected to column chromatography on silica gel (hexane:ethyl acetate=2:1) and recrystallized from ethanol to obtain 0.78 g (yield: 44.6%) of the intended product.

Workup

  1. additionwere successively added to the solution
  2. extractionextracted with ethyl acetate (150 ml×2)
  3. washwashed with a saturated saline solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was then distilled off
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-ccb86954371f4ff1a55ea60a7ab0285b
Source dataset
uspto-grants-2000_05
Patent number
US06057330

Reaction notes

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