Aluminium lithium hydride → 2-[4-(2-Ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenoxy]-ethanol

HRID 403487Notes

Reaction equation

HRID 403487 reaction equation
C[O:2][C:3](=O)[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]2[C:14]([CH2:24][CH3:25])=[N:15][N:16]3[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[N:18][C:17]=23)=[CH:8][CH:7]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:24]([C:14]1[C:13]([CH2:12][C:9]2[CH:8]=[CH:7][C:6]([O:5][CH2:4][CH2:3][OH:2])=[CH:11][CH:10]=2)=[C:17]2[N:18]=[C:19]([CH3:23])[CH:20]=[C:21]([CH3:22])[N:16]2[N:15]=1)[CH3:25]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68379074[4-(2-Ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenoxy]-acetic acid methyl ester

Product 1

HCID 683794832-[4-(2-Ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenoxy]-ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

[4-(2-Ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenoxy]-acetic acid methyl ester (9) (1.2 g, 3.40 mmol) was dissolved in 36 ml of THF. LiAlH4 (1.867 ml, 3.73 mmol) was added slowly to the reaction mixture and stirring was continued for 3 h at rt. The mixture was quenched with water and washed twice with CH2 Cl2. The aqueous layer was acidified with 1N HCl to pH3 and three times extracted with CH2 Cl2. The combined organic layers were washed with water and NaCl-solution, dried over Na2 SO4 and evaporated. The product was purified by chromatography (silica gel, chexane/ethylacetate).

Workup

  1. customThe mixture was quenched with water
  2. washwashed twice with CH2 Cl2
  3. extractionextracted with CH2 Cl2
  4. washThe combined organic layers were washed with water and NaCl-solution
  5. customdried over Na2 SO4
  6. customevaporated
  7. customThe product was purified by chromatography (silica gel, chexane/ethylacetate)

Sources & evidence

ORD record
ord-cc19547de92449b5b5292bed516912ce
Source dataset
uspto-grants-2014_06
Patent number
US08748435B2

Reaction notes

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