Ethanol → N-acetyl-N-[4-(4-acetyl-2-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidin-3-yl)pyridin-2-yl]acetamide

HRID 570147Notes

Reaction equation

HRID 570147 reaction equation
[C:1]([N:4]([C:8]1[CH:13]=[C:12]([C:14]2[C:15]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:16][N:17]3[CH:22]=[CH:21][CH:20]=[N:19][C:18]=23)[CH:11]=[CH:10][N:9]=1)[C:5](=[O:7])[CH3:6])(=[O:3])[CH3:2].[BH4-].[Na+].O.[CH2:32]([OH:34])[CH3:33]>>[C:1]([N:4]([C:8]1[CH:13]=[C:12]([C:14]2[C:15]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:16][N:17]3[CH2:22][CH2:21][CH2:20][N:19]([C:32](=[O:34])[CH3:33])[C:18]=23)[CH:11]=[CH:10][N:9]=1)[C:5](=[O:7])[CH3:6])(=[O:3])[CH3:2]

Participants

5

Reactant 4

HCID 702EthanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 89488219N-acetyl-N-[4-(2-phenylpyrazolo[1,5-a]pyrimidin-3-yl)pyridin-2-yl]acetamide

Product 1

HCID 89488227N-acetyl-N-[4-(4-acetyl-2-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidin-3-yl)pyridin-2-yl]acetamideYield 46%

Procedure

To a mixture of N-acetyl-N-[4-(2-phenylpyrazolo[1,5-a]pyrimidin-3-yl)pyridin-2-yl]acetamide (158 mg, 0.43 mmol, 1 eq) in 3 mL of ethanol is added sodium borohydride (35 mg, 0.94 mmol, 2.2 eq). The mixture is refluxed for 1 h. The mixture is then poured into water, extracted with dichloromethane (3×50 mL), dried over anhydrous magnesium sulphate, filtered and concentrated under reduced pressure. The crude material is purified by column chromatography using silica gel in heptane and ethyl acetate (1:0 to 0:1) as eluent and 66 mg (46%) of N-acetyl-N-[4-(4-acetyl-2-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidin-3-yl)pyridin-2-yl]acetamide are obtained as a white solid.

Workup

  1. temperatureThe mixture is refluxed for 1 h
  2. extractionextracted with dichloromethane (3×50 mL)
  3. dry with materialdried over anhydrous magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material is purified by column chromatography

Sources & evidence

ORD record
ord-cbe0b4a2536f4ac0900ca83b08c5a10a
Source dataset
uspto-grants-2015_05
Patent number
US09023844B2

Reaction notes

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