Methanol → 2-(1-Cyano-1-methylethylamino)-6-ethylamino-4-methoxy-5-pyrimidinecarbonitrile

HRID 372652Notes

Reaction equation

HRID 372652 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([NH:10][CH2:11][CH3:12])[N:5]=[C:4]([NH:13][C:14]([C:17]#[N:18])([CH3:16])[CH3:15])[N:3]=1.[Na].[CH3:20][OH:21]>>[C:17]([C:14]([NH:13][C:4]1[N:3]=[C:2]([O:21][CH3:20])[C:7]([C:8]#[N:9])=[C:6]([NH:10][CH2:11][CH3:12])[N:5]=1)([CH3:16])[CH3:15])#[N:18]

Participants

4

Reactant 3

HCID 887Methanol3×HCID 5360545Sodium2×HCID 538166454-Chloro-2-(1-cyano-1-methylethylamino)-6-ethylamino-5-pyrimidinecarbonitrile

Product 1

HCID 537806142-(1-Cyano-1-methylethylamino)-6-ethylamino-4-methoxy-5-pyrimidinecarbonitrile

Procedure

To a stirred solution of 2.7 grams of 4-chloro-2-(1-cyano-1-methylethylamino)-6-ethylamino-5-pyrimidinecarbonitrile in 50 ml of methanol was added a solution of 0.3 gram of sodium in 10 ml of methanol. The reaction mixture was heated under reflux for 3 hours. An additional small quantity of sodium in methanol was then added to the reaction mixture, and heating under reflux was continued for 1.5 hours. The excess methanol was removed from the reaction mixture by evaporation under reduced pressure. The residue was extracted with a mixture of diethyl ether and water. The diethyl ether layer was separated, washed with water, then dried over magnesium sulfate. The mixture was filtered, and the filtrate was evaporated under reduced pressure to a residue. The residue was washed with methylcyclohexane, and the insoluble solid was collected by filtration. The solid was recrystallized from benzene to give 1.7 grams of 2-(1-cyano-1-methylethylamino)-6-ethylamino-4-methoxy-5-pyrimidinecarbonitrile; mp, 130°-132°.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 3 hours
  3. temperatureheating
  4. temperatureunder reflux
  5. customThe excess methanol was removed from the reaction mixture by evaporation under reduced pressure
  6. extractionThe residue was extracted with a mixture of diethyl ether and water
  7. customThe diethyl ether layer was separated
  8. washwashed with water
  9. dry with materialdried over magnesium sulfate
  10. filtrationThe mixture was filtered
  11. customthe filtrate was evaporated under reduced pressure to a residue
  12. washThe residue was washed with methylcyclohexane
  13. filtrationthe insoluble solid was collected by filtration
  14. customThe solid was recrystallized from benzene

Sources & evidence

ORD record
ord-3c9c222e3db44582b42028da5b47a97f
Source dataset
uspto-grants-1978_05
Patent number
US04092150

Reaction notes

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