Triethylamine → 6-[2-(Tert-butyldimethylsilanyloxy)ethyl]-5,7-dichloropyrazolo[1,5-a]pyrimidine

HRID 1452617Notes

Reaction equation

HRID 1452617 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][CH2:9][OH:10])=[C:6]([Cl:11])[N:5]2[N:12]=[CH:13][CH:14]=[C:4]2[N:3]=1.C(N(CC)CC)C.[C:22]([Si:26](Cl)([CH3:28])[CH3:27])([CH3:25])([CH3:24])[CH3:23].[Cl-].[NH4+]>C(Cl)Cl>[Si:26]([O:10][CH2:9][CH2:8][C:7]1[C:2]([Cl:1])=[N:3][C:4]2[N:5]([N:12]=[CH:13][CH:14]=2)[C:6]=1[Cl:11])([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:28])[CH3:27]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 28928tert-Butyldimethylsilyl chlorideHCID 575268292-(5,7-Dichloropyrazolo[1,5-a]pyrimidin-6-yl)ethanol

Product 1

HCID 575268026-[2-(Tert-butyldimethylsilanyloxy)ethyl]-5,7-dichloropyrazolo[1,5-a]pyrimidineYield 108.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a methylene chloride (50 mL) solution containing 2-(5,7-dichloropyrazolo[1,5-a]pyrimidin-6-yl)ethanol (640 mg, 2.77 mmol), triethylamine (3.86 mL, 27.7 mmol) and tert-butylchlorodimethylsilane (1.25 g, 8.31 mmol) were added, and this mixture was stirred at room temperature for 16 hr. After the reaction, aqueous ammonium chloride was added to the reaction solution, and the mixture was extracted with ethyl acetate. The combined ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate and then brine and dried over sodium sulfate. After the sodium sulfate was filtered off, the solvent was distilled off and the residue was purified with column chromatography (15% ethyl acetate-hexane) to obtain the title compound (1.04 g).

Workup

  1. additionwere added
  2. additionwas added to the reaction solution
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe combined ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate
  5. dry with materialbrine and dried over sodium sulfate
  6. filtrationAfter the sodium sulfate was filtered off
  7. distillationthe solvent was distilled off
  8. customthe residue was purified with column chromatography (15% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-c289cf2202194a61afb7ccb7bf8e320c
Source dataset
uspto-grants-2009_01
Patent number
US07473694B2

Reaction notes

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