Acetic Anhydride → 1-(3-(5-bromo-2-phenylpyrimidin-4-ylamino)-5-cyclopropyl-1H-pyrazol-1-yl)ethanone

HRID 1484853Notes

Reaction equation

HRID 1484853 reaction equation
[Br:1][C:2]1[C:3]([NH:14][C:15]2[CH:19]=[C:18]([CH:20]3[CH2:22][CH2:21]3)[NH:17][N:16]=2)=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:6][CH:7]=1.[CH3:23][C:24](OC(C)=O)=[O:25]>C1COCC1.O>[Br:1][C:2]1[C:3]([NH:14][C:15]2[CH:19]=[C:18]([CH:20]3[CH2:22][CH2:21]3)[N:17]([C:24](=[O:25])[CH3:23])[N:16]=2)=[N:4][C:5]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 50943139HCID 50943139, compound

Product 1

HCID 581694581-(3-(5-bromo-2-phenylpyrimidin-4-ylamino)-5-cyclopropyl-1H-pyrazol-1-yl)ethanoneYield 67.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

To the mixture of 5-bromo-N-(5-cyclopropyl-1H-pyrazol-3-yl)-2-phenylpyrimidin-4-amine (200 mg, 0.56 mmol, 1.0 eq) in THF (8 mL) and water (5 mL) was added a solution of Ac2O (0.18 mL, 1.68 mmol, 3.0 eq) in THF (2 mL). The reaction mixture was stirred for 14 hours and water was added. The mixture was filtered and the solid was washed with water and dried by co-evaporated with ethanol to give 1-(3-(5-bromo-2-phenylpyrimidin-4-ylamino)-5-cyclopropyl-1H-pyrazol-1-yl)ethanone (150 mg, 67%). LC-MS (m/z)=398.0, 400.0 [M+H]+.

Workup

  1. filtrationThe mixture was filtered
  2. washthe solid was washed with water
  3. dry with materialdried by co-evaporated with ethanol

Sources & evidence

ORD record
ord-8157e70322714e76a85e08a44e394351
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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