Acetic Anhydride → N-(6-aminopyrimidin-4-yl)acetamide

HRID 2366202Notes

Reaction equation

HRID 2366202 reaction equation
[N:1]1[C:6]([NH2:7])=[CH:5][C:4]([NH2:8])=[N:3][CH:2]=1.[C:9](OC(=O)C)(=[O:11])[CH3:10]>O1CCOCC1>[NH2:8][C:4]1[N:3]=[CH:2][N:1]=[C:6]([NH:7][C:9](=[O:11])[CH3:10])[CH:5]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 79608Pyrimidine-4,6-diamine

Product 1

HCID 3031498N-(6-aminopyrimidin-4-yl)acetamideYield 61%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred suspension of pyrimidine-4,6-diamine (500 mg, 4.55 mmol) in dioxane (20 mL) was added acetic anhydride (465 mg, 4.55 mmol) and the resulting mixture was heated under reflux for 15 hours. The reaction was cooled to room temperature and the resulting precipitate was collected by filtration. The filtercake was dissolved in 1N HCl and the pH of the aqueous phase adjusted to 7 by the addition of 1N NaOH. The resulting white precipitate was collected by filtration and dried to afford the desired product as a white solid (420 mg, 61% yield). LCMS (ESI) m/z: 152.0 [M+H+].

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 15 hours
  3. filtrationthe resulting precipitate was collected by filtration
  4. dissolutionThe filtercake was dissolved in 1N HCl
  5. additionthe pH of the aqueous phase adjusted to 7 by the addition of 1N NaOH
  6. filtrationThe resulting white precipitate was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-df25aac569e74280ab2451790da6bd3b
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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