Sodium Methoxide → HCID 20510219, compound

HRID 372656Notes

Reaction equation

HRID 372656 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([NH:10][CH:11]([CH3:13])[CH3:12])[N:5]=[C:4]([NH:14][CH:15]([CH3:17])[CH3:16])[N:3]=1.[CH3:18][O-:19].[Na+]>CO>[CH:15]([NH:14][C:4]1[N:3]=[C:2]([O:19][CH3:18])[C:7]([C:8]#[N:9])=[C:6]([NH:10][CH:11]([CH3:13])[CH3:12])[N:5]=1)([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 20510253HCID 20510253, compound

Product 1

HCID 20510219HCID 20510219, compoundYield 121.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6.3 grams of 4-chloro-2,6-bis(isopropylamino)-5-pyrimidinecarbonitrile in 100 ml of methanol was added a solution of methanolic sodium methoxide (0.805 grams of sodium in 50 ml of methanol). After complete addition, the reaction mixture was stirred for 16 hours. The reaction mixture was then heated under reflux for 5 hours. The excess methanol was removed under reduced pressure. The residue was extracted with a mixture of diethyl ether and water. The organic layer was separated and dried over magnesium sulfate. The mixture was filtered, and the filtrate was evaporated to dryness under reduced pressure. The residue was recrystallized from cyclohexane, to give 4.5 grams of 2,6-bis(isopropylamino)-4-methoxy-5-pyrimidinecarbonitrile; mp, 131°-133°.

Workup

  1. additionAfter complete addition
  2. temperatureThe reaction mixture was then heated
  3. temperatureunder reflux for 5 hours
  4. customThe excess methanol was removed under reduced pressure
  5. extractionThe residue was extracted with a mixture of diethyl ether and water
  6. customThe organic layer was separated
  7. dry with materialdried over magnesium sulfate
  8. filtrationThe mixture was filtered
  9. customthe filtrate was evaporated to dryness under reduced pressure
  10. customThe residue was recrystallized from cyclohexane

Sources & evidence

ORD record
ord-f95e0321ce3b47fb8755b3680618336a
Source dataset
uspto-grants-1978_05
Patent number
US04092150

Reaction notes

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