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

HRID 1484846Notes

Reaction equation

HRID 1484846 reaction equation
[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[C:15]([NH2:16])=[CH:14][N:13]=[C:12]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[N:11]=3)[CH:5]=2)[CH2:3][CH2:2]1.[CH3:23][C:24](OC(C)=O)=[O:25]>>[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[C:15]([NH:16][C:24](=[O:25])[CH3:23])=[CH:14][N:13]=[C:12]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[N:11]=3)[CH:5]=2)[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 50943070N-(5-cyclopropyl-1H-pyrazol-3-yl)-2-phenyl-pyrimidine-4,5-diamine

Product 1

HCID 50943071N-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-2-phenylpyrimidin-5-yl)acetamide

Procedure

A mixture of N-(5-cyclopropyl-1H-pyrazol-3-yl)-2-phenylpyrimidine-4,5-diamine (350 mg, 1.19 mmol, 1.0 eq) and Ac2O (12 mL) was stirred at rt for 3 h and concentrated. The residue was dissolved in MeOH (3 mL). Sat. aqueous NaOH was added dropwise until pH=12 and stirred for 10 minutes. The final mixture was concentrated and purified by silica gel chromatography (hexane/EtOAc=10:1 as eluent)) to obtain target product N-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-2-phenylpyrimidin-5-yl)acetamide.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in MeOH (3 mL)
  3. additionSat. aqueous NaOH was added dropwise until pH=12
  4. stirringstirred for 10 minutes
  5. concentrationThe final mixture was concentrated
  6. custompurified by silica gel chromatography (hexane/EtOAc=10:1 as eluent))

Sources & evidence

ORD record
ord-43e0364e93e04c8991c071c39ee123c6
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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