Hydrochloric Acid → N-(4-(4-methylpyridin-2-yl)pyrimidin-2-yl)cyanamide

HRID 1059900Notes

Reaction equation

HRID 1059900 reaction equation
CN(C)[CH:3]=[CH:4][C:5]([C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][N:8]=1)=O.[C:15]([NH:17][C:18]([NH2:20])=[NH:19])#[N:16].C[O-].[Na+].Cl>C(O)C.CO>[CH3:13][C:11]1[CH:10]=[CH:9][N:8]=[C:7]([C:5]2[CH:4]=[CH:3][N:20]=[C:18]([NH:17][C:15]#[N:16])[N:19]=2)[CH:12]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 541170263-Dimethylamino-1-(4-methyl-2-pyridyl)-2-propen-1-oneHCID 178418324HCID 178418324, compound

Product 1

HCID 18667558N-(4-(4-methylpyridin-2-yl)pyrimidin-2-yl)cyanamideYield 37.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To a suspension of 3-dimethylamino-1-(4-methylpyridin-2-yl)prop-2-en-1-one (0.78 g) and cyanoguanidine (1.38 g) in ethanol (8 ml) was added a solution of sodium methoxide in methanol (28%, 1.49 ml), and the mixture was refluxed for 2 hours. The mixture was neutralized with 1N hydrochloric acid and extracted with ethyl acetate and tetrahydrofuran (3:1). The organic layer was washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 75 g, 10% methanol in dichloromethane). The solid obtained was triturated with 2-propanol, filtered and dried to give N-(4-(4-methylpyridin-2-yl)-pyrimidin-2-yl)cyanamide (325 mg).

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. extractionextracted with ethyl acetate and tetrahydrofuran (3:1)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography (silica gel 75 g, 10% methanol in dichloromethane)
  7. customThe solid obtained
  8. customwas triturated with 2-propanol
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-d8066d8a173c4c5bbde0b6936e156d75
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

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