Hydrochloric Acid → 5-Hydroxy-2-(4-benzyloxyphenyl)pyrimidine

HRID 485992Notes

Reaction equation

HRID 485992 reaction equation
C[O:2][C:3]1[CH:4]=[N:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:11][CH:10]=2)=[N:7][CH:8]=1.[OH-].[Na+].C(O)COCCO.Cl>O>[OH:2][C:3]1[CH:4]=[N:5][C:6]([C:9]2[CH:10]=[CH:11][C:12]([O:15][CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[CH:13][CH:14]=2)=[N:7][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8117Diethylene GlycolHCID 14798Sodium HydroxideHCID 190970605-Methoxy-2-(4-benzyloxyphenyl)pyrimidine

Product 1

HCID 227174625-Hydroxy-2-(4-benzyloxyphenyl)pyrimidineYield 91.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 8.42 g of 5-methoxy-2-(4-benzyloxyphenyl)pyrimidine, 6.9 g of sodium hydroxide, and 84 ml of diethylene glycol was heated at 190° to 200° C. for 2 hours. After cooling, the reaction mixture was poured into 300 ml of water, neutralized with a 1% hydrochloric acid aqueous solution, and extracted with ethyl acetate. Distillation of the extract to remove ethyl acetate gave 7.3 g (26.2 mmol; percent yield: 91.8%) of 5-hydroxy-2-(4-benzyloxyphenyl)pyrimidine.

Workup

  1. temperaturewas heated at 190° to 200° C. for 2 hours
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. distillationDistillation of the
  5. extractionextract
  6. customto remove ethyl acetate

Sources & evidence

ORD record
ord-a1171b3c2a284f268db01ccea617bfed
Source dataset
uspto-grants-1994_03
Patent number
US05290477

Reaction notes

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