Dimethyl malonate → HCID 178424666, compound

HRID 1668664Notes

Reaction equation

HRID 1668664 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]([NH2:10])=[NH:9])[CH:5]=[CH:4][CH:3]=1.[C:11](OC)(=[O:17])[CH2:12][C:13](OC)=[O:14].C[O-].[Na+]>CO>[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[N:10]=[C:13]([OH:14])[CH:12]=[C:11]([OH:17])[N:9]=2)[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7943Dimethyl malonateHCID 10942334Sodium MethoxideHCID 142532006-Methylpicolinimidamide2×

Product 1

HCID 178424666HCID 178424666, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 6-methyl-pyridine-2-carboxamidine (Intermediate B) (1.2 eq, 8.23 mmol, 1.41 g) in MeOH (5 ml) under an inert atmosphere of argon, at room temperature is treated with dimethyl malonate (1 eq, 6.86 mmol, 1.04 ml) and 0.5 M sodium methoxide in MeOH (3 eq, 20.6 mmol, 41.2 ml). The resulting mixture is heated at reflux overnight and then allowed to cool to room temperature. Silica is added and the solvent is removed in vacuo. Purification by flash chromatography eluting with 0-5% MeOH in DCM affords the title compound as a pale yellow solid; [M+H]+=204/205.

Workup

  1. temperatureThe resulting mixture is heated
  2. temperatureat reflux overnight
  3. additionSilica is added
  4. customthe solvent is removed in vacuo
  5. customPurification by flash chromatography
  6. washeluting with 0-5% MeOH in DCM

Sources & evidence

ORD record
ord-fa7b8c0e8a3f40e89a01b7e8a724353b
Source dataset
uspto-grants-2011_08
Patent number
US07989458B2

Reaction notes

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