4-Hydroxybenzaldehyde → 4-(Pyrimidin-2-yloxy)benzaldehyde

HRID 1166086Notes

Reaction equation

HRID 1166086 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1.Cl[C:13]1[N:18]=[CH:17][CH:16]=[CH:15][N:14]=1>CN(C=O)C>[N:14]1[CH:15]=[CH:16][CH:17]=[N:18][C:13]=1[O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 24758Sodium hydrideHCID 744042-Chloropyrimidine

Product 1

HCID 27635624-(Pyrimidin-2-yloxy)benzaldehydeYield 86.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

Sodium hydride (60% in oil, 1.44 g, 36.00 mmol) was added to a 0° C. solution of 4-hydroxybenzaldehyde (4.40 g, 36.03 mmol) in DMF (16 mL). After stirring for 20 min at 0° C., the mixture was allowed to warm to RT and a solution of 2-chloropyrimidine (4.12 g, 35.97 mmol) in DMF (8 mL) was added. The resulting mixture was heated to 100° C. for 18 h. The solvent was evaporated, the residue was dissolved in ethyl acetate, washed with water and brine, dried (MgSO4), and concentrated to provide 6.20 g (86%) of the title compound. MS 201 (M+H)+.

Workup

  1. temperatureto warm to RT
  2. temperatureThe resulting mixture was heated to 100° C. for 18 h
  3. customThe solvent was evaporated
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washwashed with water and brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-67c6ca92e59345f4abbebc4267ff9c53
Source dataset
uspto-grants-2003_09
Patent number
US06613747B2

Reaction notes

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