Methyl acetoacetate → HCID 178429350, compound

HRID 576918Notes

Reaction equation

HRID 576918 reaction equation
O=[C:2]([CH3:8])[CH2:3][C:4](OC)=[O:5].C[O-].[Na+].[CH3:12][NH:13][C:14]([NH2:16])=[S:15]>CO>[CH3:12][N:13]1[C:4](=[O:5])[CH:3]=[C:2]([CH3:8])[N:16]=[C:14]1[SH:15]

Participants

5

Reactant 3

HCID 7757Methyl acetoacetateHCID 2723704MethylthioureaHCID 10942334Sodium Methoxide

Product 1

HCID 178429350HCID 178429350, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 3-oxobutanoate (2 mL, 18.5 mmol) was added dropwise to a solution of sodium methoxide (25% wt in MeOH, 5 mL) and anhydrous MeOH (20 mL). N-methyl thiourea (1.67 g, 18.5 mmol) was added to the reaction mixture. The resulting solution was stirred at reflux for 5 hours. After cooling to room temperature, the solvent was evaporated. The residue was dissolved in water (25 mL), and the solution was acidified to pH 2-3 with concentrated HCl. The solid material was recovered by filtration, washed with water (2×20 mL) and diethyl ether (1×30 mL), and dried in vacuo, affording 3,6-dimethyl-2-sulfanyl-3,4-dihydropyrimidin-4-one (2.16 g, 73% yield). The product was used without further purification.

Workup

  1. temperatureat reflux for 5 hours
  2. customthe solvent was evaporated
  3. dissolutionThe residue was dissolved in water (25 mL)
  4. filtrationThe solid material was recovered by filtration
  5. washwashed with water (2×20 mL) and diethyl ether (1×30 mL)
  6. customdried in vacuo

Sources & evidence

ORD record
ord-dbb43617529840f2823f56be4f6eec12
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

Loading…