Monobenzone → 4-(4-Benzyloxy-phenoxy)-2-chloro-pyrimidine

HRID 491657Notes

Reaction equation

HRID 491657 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Cl:18][C:19]1[N:24]=[C:23](Cl)[CH:22]=[CH:21][N:20]=1>CN(C=O)C>[CH2:3]([O:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][C:21]2[CH:22]=[CH:23][N:24]=[C:19]([Cl:18])[N:20]=2)=[CH:15][CH:16]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 7638MonobenzoneHCID 24758Sodium hydrideHCID 775312,4-Dichloropyrimidine

Product 1

HCID 177554044-(4-Benzyloxy-phenoxy)-2-chloro-pyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred RT slurry of NaH (0.5 g of 60% oil dispersion, 12.6 mmol) in 15 mL DMF was added 4-benzyloxyphenol (2.40 g, 12.0 mmol). The mixture was stirred for 10 min before 2,4-dichloropyrimidine (1.79 g, 12.0 mmol) was added. A mild exotherm occurred. The reaction was stirred for 2 h and quenched with saturated aqueous NaHCO3. The reaction was diluted with EtOAc, the layers were separated, and the organic layer was washed twice with 2 N NaOH, once with brine, then dried over Na2SO4. The organic layer was filtered and concentrated in vacuo to yield crude title compound contaminated with minor impurities by H-NMR. MS (MH+)=NA; Calc'd 312.76 for C17H13ClN2O2.

Workup

  1. additionwas added
  2. customquenched with saturated aqueous NaHCO3
  3. additionThe reaction was diluted with EtOAc
  4. customthe layers were separated
  5. washthe organic layer was washed twice with 2 N NaOH, once with brine
  6. dry with materialdried over Na2SO4
  7. filtrationThe organic layer was filtered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-40dac93449dc448c8499b6c401dc640c
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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