Hydrochloric Acid → HCID 68540206, compound

HRID 1993683Notes

Reaction equation

HRID 1993683 reaction equation
C(OC(=O)[NH:7][C:8]1[N:9]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)[N:10]=[C:11]([Si:13]([CH3:16])([CH3:15])[CH3:14])[CH:12]=1)(C)(C)C.Cl.O1CCOCC1>C1COCC1>[C:20]1([CH3:23])[CH:19]=[CH:18][C:17]([N:9]2[C:8]([NH2:7])=[CH:12][C:11]([Si:13]([CH3:16])([CH3:15])[CH3:14])=[N:10]2)=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 68540442HCID 68540442, compound

Product 1

HCID 68540206HCID 68540206, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Place (2-p-tolyl-5-trimethylsilanyl-2H-pyrazol-3-yl)-carbamic acid tert-butyl ester (504 mg, 1.46 mmol) in THF (10 mL). Add 4 M HCl in dioxane (4 mL, 16 mmol) and heat to 60° C. for 3 hours. Cool the reaction to room temperature and load onto a Varian™ SCX column. Wash the column with MeOH and then flush off the product with 2 M NH3 in MeOH. Collect filtrate and concentrate under reduced pressure to yield 175 mg (49%) of 2-p-tolyl-5-trimethylsilanyl-2H-pyrazol-3-ylamine.

Workup

  1. temperatureCool
  2. customthe reaction to room temperature
  3. washWash the column with MeOH
  4. customflush off the product with 2 M NH3 in MeOH
  5. concentrationCollect filtrate and concentrate under reduced pressure

Sources & evidence

ORD record
ord-3787e58ea85b4d2e9731952671d04d4c
Source dataset
uspto-grants-2010_01
Patent number
US07652015B2

Reaction notes

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