3-Methoxyphenol → HCID 58515263, compound

HRID 1893392Notes

Reaction equation

HRID 1893392 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[CH3:10][O:11][C:12]1[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[C:3]([O:18][C:14]2[CH:15]=[CH:16][CH:17]=[C:12]([O:11][CH3:10])[CH:13]=2)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 90073-MethoxyphenolHCID 11430Potassium CarbonateHCID 2899735-Bromo-2,4-dichloropyrimidine

Product 1

HCID 58515263HCID 58515263, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 5-bromo-2,4-dichloropyrimidine (300 mg, 1.32 mmol) and 3-methoxyphenol (163.4 mg, 1.32 mmol) in DMF (5 mL) at 0° C. was added K2CO3 (363 mg, 2.63 mmol). The resulting mixture was stirred at 0° C. for 7 h. The reaction was quenched with H2O and extracted with EtOAc (3×30 mL). The combined organic extracts were washed with H2O (5×30 mL), brine, dried and concentrated. The crude product was purified by preparative TLC using 100% of CH2Cl2 as eluting solvent to afford the title compound (380 mg, 92%). 1HNMR (CDCl3, 400 MHz): 8.57 (s, 1H), 7.37 (dd, 1H), 6.88-6.84 (dd, 1H), 6.72-6.79 (dd+d, 2H), 3.83 (s, 3H). MS (ESI) m/z: Found: 315.0 (M++1), 317.0 (M++3); Calc. 314.0 (M+).

Workup

  1. customThe reaction was quenched with H2O
  2. extractionextracted with EtOAc (3×30 mL)
  3. washThe combined organic extracts were washed with H2O (5×30 mL), brine
  4. customdried
  5. concentrationconcentrated
  6. customThe crude product was purified by preparative TLC
  7. washas eluting solvent

Sources & evidence

ORD record
ord-10184444d85c492395439d726c0cee93
Source dataset
uspto-grants-2013_08
Patent number
US08513242B2

Reaction notes

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