Sodium Methoxide → 6-Cyclopropylamino-2-isopropylamino-4-methoxy-5-pyrimidinecarbonitrile

HRID 372655Notes

Reaction equation

HRID 372655 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][CH:18]([CH3:20])[CH3:19])[N:6]=1>CO>[CH:14]1([NH:13][C:9]2[N:8]=[C:7]([NH:17][CH:18]([CH3:20])[CH3:19])[N:6]=[C:5]([O:2][CH3:1])[C:10]=2[C:11]#[N:12])[CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 205102674-Chloro-6-cyclopropylamino-2-isopropylamino-5-pyrimidinecarbonitrile

Product 1

HCID 205101926-Cyclopropylamino-2-isopropylamino-4-methoxy-5-pyrimidinecarbonitrileYield 89.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 0.9 gram of sodium methoxide in 100 ml of methanol was added, in one portion, 4.0 grams of 4-chloro-6-cyclopropylamino-2-isopropylamino-5-pyrimidinecarbonitrile. The reaction mixture was then heated under reflux for 3 hours. The methanol was removed by evaporation under reduced pressure to give a residue. The residue was washed with water, and the solid was collected by filtration to yield 3.5 grams of 6-cyclopropylamino-2-isopropylamino-4-methoxy-5-pyrimidinecarbonitrile; mp, 142°-147°.

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureunder reflux for 3 hours
  3. customThe methanol was removed by evaporation under reduced pressure
  4. customto give a residue
  5. washThe residue was washed with water
  6. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-3d5b0036c46547aa81f9c6bbc8fcb2c0
Source dataset
uspto-grants-1978_05
Patent number
US04092150

Reaction notes

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