4-Methoxyphenol → HCID 58243047, compound

HRID 2359629Notes

Reaction equation

HRID 2359629 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1>CC(C)=O.C([O-])(O)=O.[Na+].O>[Cl:1][C:2]1[N:7]=[C:6]([O:20][C:17]2[CH:18]=[CH:19][C:14]([O:13][CH3:12])=[CH:15][CH:16]=2)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

Participants

6

Reactant 2

HCID 90154-MethoxyphenolHCID 5212662,4-Dichloro-5-nitropyrimidine2×

Product 1

HCID 58243047HCID 58243047, compoundYield 91.1%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 2,4-dichloro-5-nitro-pyrimidine (Compound 1a) (5.82 g; 30.0 mmol) in acetone (480 mL), cooled to 0° C., was added a solution of 4-methoxy-phenol (3.75 g; 30.0 mmol) in a mixture of 1 N NaHCO3(aq) (30 mL) and H2O (120 mL) dropwise by an addition funnel. After completion of addition, the reaction mixture was allowed to warm to ambient temperature, and was then stirred at room temperature for 3 h. The resultant mixture was evaporated in vacuo, and the residue was washed sequentially with EtOAc, 1 N NaOH(aq), and H2O. The organic phase was washed sequentially with H2O and brine, and dried over Na2SO4. The mixture was filtered and the solvent was evaporated under reduced pressure to give the crude material. The crude material was recrystallized from Et2O-hexanes to afford Compound 1b (7.70 g; 91% yield) as a yellow solid. 1H-NMR (400 MHz, CDCl3): δ 9.17 (s, 1H), 7.13-7.15 (m, 2H), 6.98-7.01 (m, 2H), 3.87 (s, 3H); MS: m/z 282.0 (M+H)+.

Workup

  1. additionAfter completion of addition
  2. customThe resultant mixture was evaporated in vacuo
  3. washthe residue was washed sequentially with EtOAc, 1 N NaOH(aq), and H2O
  4. washThe organic phase was washed sequentially with H2O and brine
  5. dry with materialdried over Na2SO4
  6. filtrationThe mixture was filtered
  7. customthe solvent was evaporated under reduced pressure
  8. customto give the crude material
  9. customThe crude material was recrystallized from Et2O-hexanes

Sources & evidence

ORD record
ord-fb726f76279f4e398f2df1aa16279be7
Source dataset
uspto-grants-2014_04
Patent number
US08685990B2

Reaction notes

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