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

HRID 584797Notes

Reaction equation

HRID 584797 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-45dd61f6f1784d72ad0dcb237cb40f95
Source dataset
uspto-grants-2005_08
Patent number
US06927221B2

Reaction notes

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