Isopropylamine → 4-Chloro-2-(1-cyano-1-methylethylamino)-6-isopropylamino-5-pyrimidinecarbonitrile

HRID 372641Notes

Reaction equation

HRID 372641 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([Cl:10])[N:5]=[C:4]([NH:11][C:12]([C:15]#[N:16])([CH3:14])[CH3:13])[N:3]=1.[CH:17]([NH2:20])([CH3:19])[CH3:18]>CC(C)=O>[Cl:10][C:6]1[C:7]([C:8]#[N:9])=[C:2]([NH:20][CH:17]([CH3:19])[CH3:18])[N:3]=[C:4]([NH:11][C:12]([C:15]#[N:16])([CH3:14])[CH3:13])[N:5]=1

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 537123174,6-Dichloro-2-(1-cyano-1-methylethylamino)-5-pyrimidinecarbonitrile

Product 1

HCID 544627074-Chloro-2-(1-cyano-1-methylethylamino)-6-isopropylamino-5-pyrimidinecarbonitrileYield 48.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 5.1 grams of 4,6-dichloro-2-(1-cyano-1-methylethylamino)-5-pyrimidinecarbonitrile in 100 ml of acetone, 2.3 grams of isopropylamine was added dropwise. The reaction mixture was then stirred at room temperature for 16 hours. The acetone was removed under reduced pressure, and the reaction mixture was extracted with a mixture of diethyl ether and water. The organic layer was separated and dried over magnesium sulfate. The solution was filtered, and the filtrate was evaporated under reduced pressure, yielding a residue. The residue was recrystallized from methylcyclohexane to give 2.7 grams of 4-chloro-2-(1-cyano-1-methylethylamino)-6-isopropylamino-5-pyrimidinecarbonitrile; mp, 144°-147°.

Workup

  1. customThe acetone was removed under reduced pressure
  2. extractionthe reaction mixture was extracted with a mixture of diethyl ether and water
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe solution was filtered
  6. customthe filtrate was evaporated under reduced pressure
  7. customyielding a residue
  8. customThe residue was recrystallized from methylcyclohexane

Sources & evidence

ORD record
ord-c25fbf0f7be94c2b84be35c159210d86
Source dataset
uspto-grants-1978_05
Patent number
US04092150

Reaction notes

Loading…