Hydrochloric Acid → {6-[3-(Tert-butyldimethylsilanyloxy)propyl]-5-chloropyrazolo[1,5-a]pyrimidin-7-yl}(4-ethoxyphenyl)amine

HRID 1452624Notes

Reaction equation

HRID 1452624 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[C:6]([Cl:24])=[N:7][C:8]2[N:9]([N:21]=[CH:22][CH:23]=2)[C:10]=1[NH:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH3:20])=[CH:14][CH:13]=1.C(N(CC)CC)C.[C:32]([Si:36](Cl)([CH3:38])[CH3:37])([CH3:35])([CH3:34])[CH3:33].Cl>C(Cl)Cl>[Si:36]([O:1][CH2:2][CH2:3][CH2:4][C:5]1[C:6]([Cl:24])=[N:7][C:8]2[N:9]([N:21]=[CH:22][CH:23]=2)[C:10]=1[NH:11][C:12]1[CH:13]=[CH:14][C:15]([O:18][CH2:19][CH3:20])=[CH:16][CH:17]=1)([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:38])[CH3:37]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 57526854[6-(3-Hydroxypropyl)-5-chloropyrazolo[1,5-a]pyrimidin-7-yl](4-ethoxyphenyl)amine

Product 1

HCID 57526823{6-[3-(Tert-butyldimethylsilanyloxy)propyl]-5-chloropyrazolo[1,5-a]pyrimidin-7-yl}(4-ethoxyphenyl)amineYield 106.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a methylene chloride (14 mL) solution containing [6-(3-hydroxypropyl)-5-chloropyrazolo[1,5-a]pyrimidin-7-yl](4-ethoxyphenyl)amine (1.43 g, 4.12 mmol), triethylamine (861 μL, 6.18 mmol) and tert-butylchlorodimethylsilane (808 mg, 5.36 mmol) were added with ice-cooling, and this mixture was stirred at room temperature for 16 hr. After the reaction, 1 mol/L hydrochloric acid was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with aqueous sodium hydrogen carbonate and then brine and dried over sodium sulfate. After the sodium sulfate was filtered off, the filtrate was concentrated and the residue was purified with column chromatography (10 to 15% ethyl acetate-hexane) to obtain the title compound (2.03 g, yield 100%).

Workup

  1. additionwere added with ice-
  2. temperaturecooling
  3. additionwas added to the reaction solution
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with aqueous sodium hydrogen carbonate
  6. dry with materialbrine and dried over sodium sulfate
  7. filtrationAfter the sodium sulfate was filtered off
  8. concentrationthe filtrate was concentrated
  9. customthe residue was purified with column chromatography (10 to 15% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-f5e270b76d4b49cd8b116a790cc203d4
Source dataset
uspto-grants-2009_01
Patent number
US07473694B2

Reaction notes

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