Hydrochloric Acid → 2-(3-Benzyloxyphenyl)-5-hydroxypyrimidine

HRID 2399198Notes

Reaction equation

HRID 2399198 reaction equation
[OH-:1].[K+].[CH2:3]([O:10][C:11]1[CH:12]=[C:13]([C:17]2[N:22]=[CH:21][C:20](Br)=[CH:19][N:18]=2)[CH:14]=[CH:15][CH:16]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O.Cl>C(O)CO.[S]>[CH2:3]([O:10][C:11]1[CH:12]=[C:13]([C:17]2[N:22]=[CH:21][C:20]([OH:1])=[CH:19][N:18]=2)[CH:14]=[CH:15][CH:16]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 193862262-(3-Benzyloxyphenyl)-5-bromopyrimidine

Product 1

HCID 193862292-(3-Benzyloxyphenyl)-5-hydroxypyrimidineYield 80.5%

Reagents, catalysts & solvents 2

HCID 5362487SulfurCatalystHCID 174Ethylene GlycolSolvent2×

Procedure

A solution of 4.76 g (85.3 mmol) of potassium hydroxide in 20 ml of ethylene glycol is added dropwise over the course of 2 hours at 180° C. to 7.26 g (21.3 mmol) of 2-(3-benzyloxyphenyl)-5-bromopyrimidine and 0.035 g (1.08 mmol) of sulfur in 60 ml of ethylene glycol. The mixture is kept at 180° C. for a further 3 hours, poured into water and acidified by means of 37% strength hydrochloric acid, and the solid which precipitates is isolated by filtration. Purification by chromatography (silica gel/hexane: ethyl acetate=32) gives 4.77 g of 2-(3-benzyloxyphenyl)-5-hydroxypyrimidine. ##STR28##

Workup

  1. customthe solid which precipitates
  2. customis isolated by filtration
  3. customPurification by chromatography (silica gel/hexane: ethyl acetate=32)

Sources & evidence

ORD record
ord-c620392374114fb480d4544d161143b6
Source dataset
uspto-grants-1995_09
Patent number
US05447656

Reaction notes

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