Water → HCID 67260840, compound

HRID 2359043Notes

Reaction equation

HRID 2359043 reaction equation
C([NH:8][C:9]1[N:14]=[C:13]([C:15]2[C:16]([C:23]3[S:24][C:25]([Cl:28])=[CH:26][CH:27]=3)=[N:17][N:18]([CH:20]([CH3:22])[CH3:21])[CH:19]=2)[CH:12]=[CH:11][N:10]=1)C1C=CC=CC=1.O.[OH-].[Na+]>S(=O)(=O)(O)O>[Cl:28][C:25]1[S:24][C:23]([C:16]2[C:15]([C:13]3[CH:12]=[CH:11][N:10]=[C:9]([NH2:8])[N:14]=3)=[CH:19][N:18]([CH:20]([CH3:22])[CH3:21])[N:17]=2)=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 67261084HCID 67261084, compound

Product 1

HCID 67260840HCID 67260840, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A mixture of N-benzyl-4-[3-(5-chloro-2-thienyl)-1-isopropyl-1H-pyrazol-4-yl]pyrimidin-2-amine (1 eq, 3.1 mmol) in 11 mL sulfuric acid was stirred at room temperature overnight. Ice was added followed by water and a solution of NaOH 30% until pH=9. The aqueous layer was extracted with dichloromethane and the combined organic extracts were dried over MgSO4 filtered and concentrated to afford 0.55 g of 4-[3-(5-chloro-2-thienyl)-1-isopropyl-1H-pyrazol-4-yl]pyrimidin-2-amine (50% yield).

Workup

  1. additionIce was added
  2. extractionThe aqueous layer was extracted with dichloromethane
  3. dry with materialthe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-26f02fa6538a4d438475e6319514e3d6
Source dataset
uspto-grants-2014_04
Patent number
US08685974B2

Reaction notes

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