3-Hydroxybenzaldehyde → 3-(Pyrimidin-2-yloxy)benzaldehyde

HRID 1280287Notes

Reaction equation

HRID 1280287 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].Cl[C:11]1[N:16]=[CH:15][CH:14]=[CH:13][N:12]=1.C([O-])([O-])=O.[K+].[K+].O>CS(C)=O>[N:12]1[CH:13]=[CH:14][CH:15]=[N:16][C:11]=1[O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6]

Participants

6

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 962WaterHCID 11430Potassium CarbonateHCID 744042-Chloropyrimidine

Product 1

HCID 27633363-(Pyrimidin-2-yloxy)benzaldehydeYield 71%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

EX-605A) A slurry of 3-hydroxybenzaldehyde (1.22 g, 10 mmol), 2-chloropyrimidine (1.14 g, 10 mmol) and K2CO3 (1.65 g, 12 mmol) in DMSO (20 mL) was heated to 100° C. for 1 h. The cooled mixture was poured into water and extracted with Et2O. The organic layer was washed with 2.5 N NaOH, 1 N HCl, saturated NaHCO3 and brine, dried (MgSO4) and evaporated to yield 1.42 g (71%) of the desired 3-(2-pyrimidinyl-oxy)benzaldehyde product as a white solid which was used without further purification. 1H NMR (C6D6) δ 7.12 (t, 1H), 7.54 (m, 1H), 7.66 (t, 1H), 7.78 (m, 1H), 7.83 (m, 1H), 8.64 (d, 2H), 10.05 (s, 1H).

Workup

  1. extractionextracted with Et2O
  2. washThe organic layer was washed with 2.5 N NaOH, 1 N HCl, saturated NaHCO3 and brine
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-92ec8d1b2091413aa5118ac7c8ff9f63
Source dataset
uspto-grants-2002_09
Patent number
US06448295B1

Reaction notes

Loading…