Water → 4-(7-(Butyl)-3-mesityl-2,5-dimethylpyrazolo[1,5-a]pyrimidin-yl)-1-butanol

HRID 966004Notes

Reaction equation

HRID 966004 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH2:11]([C:15]1[N:20]2[N:21]=[C:22]([CH3:33])[C:23]([C:24]3[C:29]([CH3:30])=[CH:28][C:27]([CH3:31])=[CH:26][C:25]=3[CH3:32])=[C:19]2[N:18]=[C:17]([CH3:34])[C:16]=1[CH2:35][CH2:36][CH2:37][C:38](OCC)=[O:39])[CH2:12][CH2:13][CH3:14].C(OCC)(=O)C.O>CCCCCC.O1CCCC1>[CH2:11]([C:15]1[N:20]2[N:21]=[C:22]([CH3:33])[C:23]([C:24]3[C:25]([CH3:32])=[CH:26][C:27]([CH3:31])=[CH:28][C:29]=3[CH3:30])=[C:19]2[N:18]=[C:17]([CH3:34])[C:16]=1[CH2:35][CH2:36][CH2:37][CH2:38][OH:39])[CH2:12][CH2:13][CH3:14]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 21225700DiisobutylaluminumhydrideHCID 22249666Ethyl 4-(7-(butyl)-3-mesityl-2,5-dimethylpyrazolo[1,5-a]pyrimidin-6-yl)butanoate

Product 1

HCID 222495124-(7-(Butyl)-3-mesityl-2,5-dimethylpyrazolo[1,5-a]pyrimidin-yl)-1-butanolYield 114.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A 1.0M solution of diisobutylaluminium hydride in hexane was added dropwise into a solution of ethyl 4-(7-(butyl)-3-mesityl-2,5-dimethylpyrazolo[1,5-a]pyrimidin-6-yl)butanoate (320 mg, 0.71 mmol) in tetrahydrofuran (10 mL) under nitrogen stream, followed by stirring for 30 minutes. After Celite was added, the mixture was treated by adding ethyl acetate and water dropwise, and the insoluble matters were filtered off. The solution was extracted with ethyl acetate, dried over anhydrous magnesium sulfate and evaporated, to give the title compound (320 mg) as a brown oil.

Workup

  1. additionAfter Celite was added
  2. additionthe mixture was treated
  3. filtrationthe insoluble matters were filtered off
  4. extractionThe solution was extracted with ethyl acetate
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-aa07ee062bf94fddb895329db10a0145
Source dataset
uspto-grants-2005_10
Patent number
US06951865B2

Reaction notes

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