Potassium Carbonate → 2-[(4-Acetyl-3-hydroxy-2-propylbenzyl)thio]-4-hydroxypyrimidine

HRID 1381582Notes

Reaction equation

[C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Cl)=[C:6]([CH2:12][CH2:13][CH3:14])[C:5]=1[OH:15])(=[O:3])[CH3:2].[OH:16][C:17]1[CH:22]=[CH:21][N:20]=[C:19]([SH:23])[N:18]=1.C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C.C(C(C)=O)C>[C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][S:23][C:19]2[N:18]=[C:17]([OH:16])[CH:22]=[CH:21][N:20]=2)=[C:6]([CH2:12][CH2:13][CH3:14])[C:5]=1[OH:15])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of 0.30 g of 4-acetyl-3-hydroxy-2-propylbenzyl chloride, 0.20 g of 4-hydroxy-2-mercaptopyrimidine, 0.20 g of anhydrous potassium carbonate and 4 ml of methyl ethyl ketone was added a catalytic amount of tetra-n-butylammonium bromide. The mixture was stirred at 60° C. for 1 day. A 1N aqueous sodium hydroxide solution and ethyl acetate were added to the reaction mixture to fractionate. The organic phase was dried over anhydrous magnesium sulfate, the solvent was distilled off. The residue was applied to silica gel column chromatography. Elution with a mixture of hexane-ethyl acetate (1:2) gave 0.10 g of 2-[(4-acetyl-3- hydroxy-2-propylbenzyl)thio]-4-hydroxypyrimidine.

Workup

dry with materialThe organic phase was dried over anhydrous magnesium sulfate
distillationthe solvent was distilled off
washElution
additionwith a mixture of hexane-ethyl acetate (1:2)

Sources & evidence

ORD record: ord-354d97ff37fd498e8d055109b917ef5d
Source dataset: uspto-grants-1989_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04803211

Reaction notes

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