Potassium tert-butoxide → HCID 178494135, compound

HRID 474571Notes

Reaction equation

HRID 474571 reaction equation
[CH:1]([CH:3]([CH2:8][C:9]1[CH:10]=[N:11][C:12]([O:15][CH3:16])=[N:13][CH:14]=1)[C:4]([O:6]C)=O)=O.CC(C)([O-])C.[K+].[N+:23]([NH:26][C:27]([NH2:29])=[NH:28])([O-:25])=[O:24]>C(O)C>[CH3:16][O:15][C:12]1[N:11]=[CH:10][C:9]([CH2:8][C:3]2[C:4](=[O:6])[N:28]=[C:27]([NH:26][N+:23]([O-:25])=[O:24])[NH:29][CH:1]=2)=[CH:14][N:13]=1

Participants

5

Reactant 3

HCID 23665647Potassium tert-butoxideHCID 86287517NitroguanidineHCID 86666188Methyl 2-formyl-3-(2-methoxypyrimidin-5-yl)propanoate

Product 1

HCID 178494135HCID 178494135, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

To the solution of methyl 2-formyl-3-[2-(methyloxy)-5-pyrimidinyl]propanoate (2 g, 8.92 mmol) and potassium tert-butoxide (3.00 g, 26.8 mmol) in ethanol (15 mL) was added neat N-nitroguanidine (1.857 g, 17.84 mmol). The reaction mixture was stirred at 120° C. for 1 h. After removing the solvent, 5 mL water was added to dissolve the solid, and HCl (conc.) was used to adjust pH ˜3. The precipitate was collected to provide the title compound (1.8 g, 72.5% yield). LCMS: rt=0.96 min, [M+1-H+]=279.1

Workup

  1. customAfter removing the solvent, 5 mL water
  2. additionwas added
  3. dissolutionto dissolve the solid, and HCl (conc.)
  4. customThe precipitate was collected

Sources & evidence

ORD record
ord-ba3a22529b8546b0bfef7b69e0da40e4
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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