Water → 4-(2-Phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidin-3-yl)pyridin-2-amine

HRID 570144Notes

Reaction equation

HRID 570144 reaction equation
[C:1]1([C:7]2[C:15]([C:16]3[CH:21]=[CH:20][N:19]=[C:18]([NH2:22])[CH:17]=3)=[C:10]3[N:11]=[CH:12][CH:13]=[CH:14][N:9]3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].O>C(O)C>[C:1]1([C:7]2[C:15]([C:16]3[CH:21]=[CH:20][N:19]=[C:18]([NH2:22])[CH:17]=3)=[C:10]3[NH:11][CH2:12][CH2:13][CH2:14][N:9]3[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 894883724-(2-Phenylpyrazolo[1,5-a]pyrimidin-3-yl)pyridin-2-amine

Product 1

HCID 1365061704-(2-Phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidin-3-yl)pyridin-2-amineYield 49.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 4-(2-phenylpyrazolo[1,5-a]pyrimidin-3-yl)pyridin-2-amine (60 mg, 0.2 mmol, 1 eq) in 3 mL of ethanol is added sodium borohydride (17 mg, 0.45 mmol, 2.2 eq). The mixture is stirred at room temperature for 2 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. 29 mg (47%) of 4-(2-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidin-3-yl)pyridin-2-amine are obtained as a white solid which is used in the next step without further purification.

Workup

  1. extractionextracted with dichloromethane (3×50 mL)
  2. dry with materialdried over anhydrous magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-08835f14e2cd46918a877973c688d183
Source dataset
uspto-grants-2015_05
Patent number
US09023844B2

Reaction notes

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