Monobenzone → 5-(p-Hydroxyphenoxy)pyrimidine

HRID 76130

Reaction equation

HRID 76130 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1C=CC=CC=1.BrC1[CH:18]=[N:19][CH:20]=[N:21]C=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.O>[OH:15][C:12]1[CH:11]=[CH:10][C:9]([O:8][C:1]2[CH:2]=[N:21][CH:20]=[N:19][CH:18]=2)=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 7638MonobenzoneHCID 10796Cesium carbonateHCID 783445-Bromopyrimidine

Product 1

HCID 129406205-(p-Hydroxyphenoxy)pyrimidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To 1.00 g (4.99 mmol) 4-(benzyloxy)phenol and 794 mg (4.99 mmol) 5-bromo-pyrimidine in 5 mL DMF are added 3.25 g (9.99 mmol) Cs2CO3 and the reaction mixture is stirred at 120° C. for 6 h in a microwave oven. Then the reaction mixture is diluted with water and extracted with EtOAc. The organic layer is dried with Na2SO4 and the solvent is removed in vacuo. The residue is purified by HPLC (MeOH/H2O/NH3).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer is dried with Na2SO4
  3. customthe solvent is removed in vacuo
  4. customThe residue is purified by HPLC (MeOH/H2O/NH3)

Sources & evidence

ORD record
ord-e7978093a2dc4120954dbcd795fa8f7e
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Linked notes

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