4-(4-Chloro-2-phenyl-5-pyrimidinyl)-o-phenylene diacetate → 5-(3,4-dihydroxyphenyl)-2-phenyl-4(3H)-pyrimidinethione

HRID 1755850Notes

Reaction equation

HRID 1755850 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12](Cl)=[N:13][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:15][CH:16]=2)=[CH:7][C:6]=1[O:24]C(=O)C)(=O)C.O.[SH2:29].[Na]>CO>[OH:24][C:6]1[CH:7]=[C:8]([C:11]2[C:12](=[S:29])[NH:13][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:15][CH:16]=2)[CH:9]=[CH:10][C:5]=1[OH:4]

Participants

4

Reactant 2

HCID 218053654-(4-Chloro-2-phenyl-5-pyrimidinyl)-o-phenylene diacetateHCID 53442613Sodium hydrogen sulfide hydrate

Product 1

HCID 199179865-(3,4-dihydroxyphenyl)-2-phenyl-4(3H)-pyrimidinethioneYield 77.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-(4-Chloro-2-phenyl-5-pyrimidinyl)-o-phenylene diacetate (6.0 g) (15.7 mmol) are suspended in 200 ml of methanol. 10 g of sodium hydrogen sulphide hydrate are added at 50° C. while stirring. After a further 4 hours at 60° C. the mixture is filtered and the filtrate is concentrated. The residue is dissolved in about 150 ml of water and the solution is brought to pH 5 with 1N aqueous hydrochloric acid. The precipitated product is filtered off under suction, washed with water, dried at room temperature and crystallized from ethanol. There are obtained 3.6 g of 5-(3,4-dihydroxyphenyl)-2-phenyl-4(3H)-pyrimidinethione as yellow crystals of m.p. 220° C.

Workup

  1. filtrationAfter a further 4 hours at 60° C. the mixture is filtered
  2. concentrationthe filtrate is concentrated
  3. dissolutionThe residue is dissolved in about 150 ml of water
  4. filtrationThe precipitated product is filtered off under suction
  5. washwashed with water
  6. customdried at room temperature
  7. customcrystallized from ethanol

Sources & evidence

ORD record
ord-ddb043fdda33463aae58ef6dca849e18
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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