Sodium Methoxide → HCID 54271917, compound

HRID 372654Notes

Reaction equation

HRID 372654 reaction equation
[CH3:1][O-:2].[Na+].Cl[C:5]1[C:10]([C:11]#[N:12])=[C:9]([NH:13][CH:14]2[CH2:16][CH2:15]2)[N:8]=[C:7]([NH:17][C:18]([C:21]#[N:22])([CH3:20])[CH3:19])[N:6]=1>CO>[C:21]([C:18]([NH:17][C:7]1[N:6]=[C:5]([O:2][CH3:1])[C:10]([C:11]#[N:12])=[C:9]([NH:13][CH:14]2[CH2:16][CH2:15]2)[N:8]=1)([CH3:20])[CH3:19])#[N:22]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 53711944HCID 53711944, compound

Product 1

HCID 54271917HCID 54271917, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 0.8 gram of sodium methoxide in 100 ml of methanol was added portionwise 4.2 grams of 4-chloro-2-(1-cyano-1-methylethylamino)-6-cyclopropylamino-5-pyrimidinecarbonitrile. Upon complete addition, the reaction mixture was heated under reflux for 3.5 hours, then allowed to stand at room temperature for 16 hours. The methanol was removed by evaporation under reduced pressure. The residue was extracted with a mixture of water and methylene chloride. The methylene chloride layer was separated and dried over magnesium sulfate. The mixture was filtered, and the filtrate was evaporated under reduced pressure. The residue was recrystallized twice from carbon tetrachloride to give 2.4 grams of 2-(1-cyano-1-methylethylamino)-6-cyclopropylamino-4-methoxy-5-pyrimidinecarbonitrile; mp, 138°-140°.

Workup

  1. additionUpon complete addition
  2. temperaturethe reaction mixture was heated
  3. temperatureunder reflux for 3.5 hours
  4. customThe methanol was removed by evaporation under reduced pressure
  5. extractionThe residue was extracted with a mixture of water and methylene chloride
  6. customThe methylene chloride layer was separated
  7. dry with materialdried over magnesium sulfate
  8. filtrationThe mixture was filtered
  9. customthe filtrate was evaporated under reduced pressure
  10. customThe residue was recrystallized twice from carbon tetrachloride

Sources & evidence

ORD record
ord-3193a9faf4db4eba81ba84bfa3f7d5df
Source dataset
uspto-grants-1978_05
Patent number
US04092150

Reaction notes

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