Water → HCID 21475296, compound

HRID 2294534Notes

Reaction equation

HRID 2294534 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]([C:11]1[CH:12]=[C:13]([NH:22][C:23]2[N:28]3[N:29]=[CH:30][C:31]([C:32](OCC)=[O:33])=[C:27]3[N:26]=[C:25]([CH3:37])[CH:24]=2)[CH:14]=[C:15]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:16]=1[OH:17])([CH3:10])([CH3:9])[CH3:8].C(OCC)(=O)C.O>CCOCC.C1COCC1>[C:7]([C:11]1[CH:12]=[C:13]([NH:22][C:23]2[N:28]3[N:29]=[CH:30][C:31]([CH2:32][OH:33])=[C:27]3[N:26]=[C:25]([CH3:37])[CH:24]=2)[CH:14]=[C:15]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:16]=1[OH:17])([CH3:8])([CH3:9])[CH3:10]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydride2×HCID 21475301HCID 21475301, compound

Product 1

HCID 21475296HCID 21475296, compoundYield 72.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of LiAlH4 (840 mg) in anhydrous ether (50 ml) is added dropwise a solution of 7-(3,5-di-t-butyl-4-hydroxyphenyl)amino-3-ethoxycarbonyl-5-methyl-pyrazolo[1,5-a]pyrimidine (3.5 g) prepared in Example 10 in dry THF (50 ml) with ice-cooling, and the mixture is stirred at the same temperature for 30 minutes, and further stirred at room temperature for one hour. To the mixture are added ethyl acetate and water to decompose excess LiAlH4, and the mixture is filtered with celite. The filtrate is diluted with ethyl acetate, and washed with a saturated aqueous Na2S2 O4 solution and a saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. The mixture is evaporated to remove the solvent, and the residue is purified by silica gel column chromatography (solvent; ethyl acetate/dichloroethane=2:1→chloroform/methanol=8:1). The obtained crystal is washed with ethyl ether to give 7-(3,5-di-t-butyl-4-hydroxyphenyl)amino-3-hydroxymethyl-5-methylpyrazolo[1,5-a]pyrimidine (2.3 g) as colorless crystal.

Workup

  1. temperaturecooling
  2. stirringfurther stirred at room temperature for one hour
  3. filtrationthe mixture is filtered with celite
  4. additionThe filtrate is diluted with ethyl acetate
  5. washwashed with a saturated aqueous Na2S2 O4 solution
  6. dry with materiala saturated sodium chloride solution, and dried over anhydrous magnesium sulfate
  7. customThe mixture is evaporated
  8. customto remove the solvent
  9. customthe residue is purified by silica gel column chromatography (solvent; ethyl acetate/dichloroethane=2:1→chloroform/methanol=8:1)
  10. washThe obtained crystal is washed with ethyl ether

Sources & evidence

ORD record
ord-5daac717c1e64907bfaa52efea50821e
Source dataset
uspto-grants-1997_11
Patent number
US05688949

Reaction notes

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