Methyl formate → 5-[(1-methyl-1H-pyrazol-4-yl)methyl]-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone

HRID 705934Notes

Reaction equation

HRID 705934 reaction equation
CC(C)([O-])C.[K+].[CH3:7][N:8]1[CH:12]=[C:11]([CH2:13][CH2:14][C:15]([O:17]C)=O)[CH:10]=[N:9]1.[CH:19](OC)=O.[NH2:23][C:24]([NH2:26])=[S:25]>C1COCC1.CO>[CH3:7][N:8]1[CH:12]=[C:11]([CH2:13][C:14]2[C:15](=[O:17])[NH:23][C:24](=[S:25])[NH:26][CH:19]=2)[CH:10]=[N:9]1

Participants

7

Reactant 4

HCID 7865Methyl formateHCID 2723790ThioureaHCID 21936147Methyl 3-(1-methyl-1H-pyrazol-4-yl)propanoateHCID 23665647Potassium tert-butoxide

Product 1

HCID 219363855-[(1-methyl-1H-pyrazol-4-yl)methyl]-2-thioxo-2,3-dihydro-4(1H)-pyrimidinoneYield 50.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred ice-cooled solution of potassium tert-butoxide (8.41 g, 74.9 mmol) in dry THF (150 mL) under argon was added dropwise a solution of methyl 3-(1-methyl-1H-pyrazol-4-yl)propanoate (4.2 g, 24.97 mmol) and methyl formate (4.50 g, 74.9 mmol) in THF (150 mL). The mixture was then allowed to warm to room temperature and stirring continued overnight. After removing the solvent, thiourea (1.901 g, 24.97 mmol) and methanol (100 mL) was added. The mixture was heated at 50° C. overnight. After removing the solvent, water (10 mL) was added. and acidified to pH 3 with HCl. The mixture was stirred in ice bath for 1 h. Filtration then drying in vacuo at 50° C. overnight then afforded the title compound (2.8 g, 12.60 mmol, 50.4% yield). LCMS: rt=0.99 min, [M+H]=223

Workup

  1. additionwas added
  2. temperatureThe mixture was heated at 50° C. overnight
  3. customAfter removing the solvent, water (10 mL)
  4. additionwas added
  5. stirringThe mixture was stirred in ice bath for 1 h
  6. filtrationFiltration
  7. customthen drying in vacuo at 50° C. overnight

Sources & evidence

ORD record
ord-49cb4cb9ff8645278c0596e5b5e843a5
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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