Water → N-acetyl-N-[4-(2-phenylpyrazolo[1,5-a]pyrimidin-3-yl)pyridin-2-yl]acetamide

HRID 570146Notes

Reaction equation

HRID 570146 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.C(N([CH2:28][CH3:29])CC)C.[C:30](Cl)(=[O:32])[CH3:31].[OH2:34]>O1CCCC1>[C:30]([N:22]([C:18]1[CH:17]=[C:16]([C:15]2[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[N:8][N:9]3[CH:14]=[CH:13][CH:12]=[N:11][C:10]=23)[CH:21]=[CH:20][N:19]=1)[C:28](=[O:34])[CH3:29])(=[O:32])[CH3:31]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 894883724-(2-Phenylpyrazolo[1,5-a]pyrimidin-3-yl)pyridin-2-amine

Product 1

HCID 89488219N-acetyl-N-[4-(2-phenylpyrazolo[1,5-a]pyrimidin-3-yl)pyridin-2-yl]acetamideYield 37%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(2-phenylpyrazolo[1,5-a]pyrimidin-3-yl)pyridin-2-amine (420 mg, 1.46 mmol, 1 eq) in 20 mL of tetrahydrofurane is added triethylamine (0.82 mL, 5.85 mmol, 4 eq) and then acetyl chloride (234 mg, 2.92 mmol, 2 eq). The mixture is stirred overnight at room temperature and then poured into water and extracted with dichloromethane (3×50 mL). The combined organic layers are washed with a saturated solution of NaHCO3, brine, 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 0.23 g (37%) of N-acetyl-N-[4-(2-phenylpyrazolo[1,5-a]pyrimidin-3-yl)pyridin-2-yl]acetamide are obtained as a yellow solid.

Workup

  1. extractionextracted with dichloromethane (3×50 mL)
  2. washThe combined organic layers are washed with a saturated solution of NaHCO3, brine
  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-835157fea8654c90a685e24f54f137f7
Source dataset
uspto-grants-2015_05
Patent number
US09023844B2

Reaction notes

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