Water → HCID 135829374, compound

HRID 916594Notes

Reaction equation

HRID 916594 reaction equation
Cl.[C:2]([NH2:5])(=[NH:4])[CH3:3].C[O-].[Na+].[CH2:9]([S:11][C:12]1[CH:26]=[CH:25][C:15]([CH2:16][CH:17]([C:22]([CH3:24])=O)[C:18](OC)=[O:19])=[CH:14][CH:13]=1)[CH3:10].O>CO>[CH2:9]([S:11][C:12]1[CH:26]=[CH:25][C:15]([CH2:16][C:17]2[C:18](=[O:19])[NH:4][C:2]([CH3:3])=[N:5][C:22]=2[CH3:24])=[CH:14][CH:13]=1)[CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 67170Acetamidine monohydrochlorideHCID 10942334Sodium MethoxideHCID 22934970HCID 22934970, compound

Product 1

HCID 135829374HCID 135829374, compoundYield 21.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 4-ethylthiobenzyl alcohol (3.7 g) in tetrahydrofuran (80 mL) were added triethylamine (3.0 mL) and methanesulfonyl chloride (1.7 mL) at 0° C., and the mixture was stirred for 30 minutes. After the insoluble material was removed by filtration, the filtrate was added to a suspension of sodium hydride (60%, 0.88 g) and methyl acetoacetate (2.4 mL) in 1,2-dimethoxyethane (100 mL), and the mixture was heated under reflux for 4 hours. The reaction mixture was poured into saturated aqueous sodium bicarbonate solution, and the mixture was extracted with diethyl ether. The organic layer was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was removed to give methyl 2-(4-ethylthiobenzyl)-acetoacetate (6.1 g). To a suspension of acetoamidine hydrochloride (0.80 g) in methanol (15 mL) was added sodium methoxide (28% solution in methanol, 1.7 mL), and the mixture was stirred for 5 minutes at room temperature. To the reaction mixture was added a solution of methyl 2-(4-ethylthiobenzyl)-acetoacetate (1.5 g) in methanol (5 mL), and the mixture was stirred for 18 hours at room temperature. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. To the residue was added ethyl acetate, and the resulting precipitated crystals were collected by filtration and dried to give 5-(4-ethylthiobenzyl)-2,6-dimethyl-3H-pyrimidin-4-one (0.33 g).

Workup

  1. stirringthe mixture was stirred for 18 hours at room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. additionTo the residue was added ethyl acetate
  6. customthe resulting precipitated crystals
  7. filtrationwere collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-9577a826695f4a2891b89388b46ec713
Source dataset
uspto-grants-2007_09
Patent number
US07271153B2

Reaction notes

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