Cesium carbonate → 2-(2-Methoxy-4-nitrophenoxy)pyrimidine

HRID 38244

Reaction equation

HRID 38244 reaction equation
Br[C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:8][O:9][C:10]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:11]=1[OH:19].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH3:8][O:9][C:10]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:11]=1[O:19][C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 767382-Methoxy-4-nitrophenolHCID 783452-Bromopyrimidine

Product 1

HCID 674400092-(2-Methoxy-4-nitrophenoxy)pyrimidineYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

According to Scheme 3 Step 1 Method B: 2-Bromopyrimidine (1.26 mmol, 211 mg) was added to a suspension of 2-methoxy-4-nitrophenol (1.15 mmol, 200 mg), Cs2CO3 (1.41 mmol, 460 mg) in DMF (3 mL). The reaction mixture was stirred at 80° C. for 3 days. The reaction mixture was quenched with water. The aqueous phase was extracted with AcOEt. The organic phase was washed with brine, was dried over MgSO4, was filtered and was concentrated under reduced pressure. The crude product was washed with a solution of NaOH 3M and dried to obtain 2-(2-methoxy-4-nitrophenoxy)pyrimidine (0.89 mmol, 220 mg, 78%) as a solid. The product was used without further purification.

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionThe aqueous phase was extracted with AcOEt
  3. washThe organic phase was washed with brine
  4. dry with materialwas dried over MgSO4
  5. filtrationwas filtered
  6. concentrationwas concentrated under reduced pressure
  7. washThe crude product was washed with a solution of NaOH 3M
  8. customdried

Sources & evidence

ORD record
ord-253ba729488a49fd979764e8aac6fb34
Source dataset
uspto-grants-2013_09
Patent number
US08524726B2

Linked notes

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