4-(4-Chloro-5-pyrimidinyl)-o-phenylene diacetate → 5-(3,4-dihydroxyphenyl)-4(3H)-pyrimidinethione

HRID 1755859Notes

Reaction equation

HRID 1755859 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12](Cl)=[N:13][CH:14]=[N:15][CH:16]=2)=[CH:7][C:6]=1[O:18]C(=O)C)(=O)C.O.[SH2:23].[Na]>CO>[OH:18][C:6]1[CH:7]=[C:8]([C:11]2[C:12](=[S:23])[NH:13][CH:14]=[N:15][CH:16]=2)[CH:9]=[CH:10][C:5]=1[OH:4]

Participants

4

Reactant 2

HCID 218054064-(4-Chloro-5-pyrimidinyl)-o-phenylene diacetateHCID 53442613Sodium hydrogen sulfide hydrate

Product 1

HCID 199178705-(3,4-dihydroxyphenyl)-4(3H)-pyrimidinethioneYield 97.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

4-(4-Chloro-5-pyrimidinyl)-o-phenylene diacetate (1.1 g) (3.6 mmol) are dissolved in 30 ml of methanol. 1.56 g of sodium hydrogen sulphide hydrate are added thereto and the mixture is stirred at 60° C. for 4.5 hours. The solvent is distilled off in a vacuum and the residue is dissolved in 20 ml of water. The solution is acidified with dilute aqueous hydrochloric acid to pH 5, the precipitated product is filtered off under suction and washed with water and diethyl ether. After drying in a high vacuum there are obtained 770 mg of 5-(3,4-dihydroxyphenyl)-4(3H)-pyrimidinethione as yellow crystals of m.p. 235° C. (dec.).

Workup

  1. distillationThe solvent is distilled off in a vacuum
  2. dissolutionthe residue is dissolved in 20 ml of water
  3. filtrationthe precipitated product is filtered off under suction
  4. washwashed with water and diethyl ether
  5. customAfter drying in a high vacuum

Sources & evidence

ORD record
ord-f181397c4013493983b720e1d437bd57
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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