Acetic Anhydride → HCID 57929452, compound

HRID 2386677Notes

Reaction equation

HRID 2386677 reaction equation
C[Mg]Br.[CH:4]1([NH:8][C:9]2[C:14]([C:15]#[N:16])=[CH:13][N:12]=[C:11]([S:17][CH3:18])[N:10]=2)[CH2:7][CH2:6][CH2:5]1.[CH3:19][C:20](OC(C)=O)=[O:21]>C1(C)C=CC=CC=1>[C:15]([C:14]1[C:9]([N:8]([CH:4]2[CH2:5][CH2:6][CH2:7]2)[C:20](=[O:21])[CH3:19])=[N:10][C:11]([S:17][CH3:18])=[N:12][CH:13]=1)#[N:16]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 57929464HCID 57929464, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 57929452HCID 57929452, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of methyl magnesium bromide (3.0 M in Et2O, 0.58 mL, 1.75 mmol) was added, at RT, to a solution of 4-cyclobutylamino-2-methylsulfanyl-pyrimidine-5-carbonitrile (350 mg, 1.59 mmol) in toluene (32 mL) and the resulting mixture was stirred for 30 min. Ac2O (3.0 mL, 31.8 mmol) was then added and the reaction mixture was heated at reflux for 5 days. The reaction mixture was then cooled to RT, quenched with water (100 mL) and extracted with EtOAc (2×100 mL). The combined organic extracts were dried over MgSO4, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography (EtOAc/hexane, 0/100 to 30/70 in 10 min) to afford 207 mg (50% yield) of N-(5-cyano-2-methylsulfanyl-pyrimidin-4-yl)-N-cyclobutyl-acetamide as a yellow solid.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 5 days
  3. customquenched with water (100 mL)
  4. extractionextracted with EtOAc (2×100 mL)
  5. dry with materialThe combined organic extracts were dried over MgSO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe crude residue was purified by flash chromatography (EtOAc/hexane, 0/100 to 30/70 in 10 min)

Sources & evidence

ORD record
ord-28cdae784cd04ccfa488b70fc20a04df
Source dataset
uspto-grants-2012_09
Patent number
US08268840B2

Reaction notes

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