Ethylamine → 4-Chloro-6-ethylamino-2-isopropylamino-5-pyrimidinecarbonitrile

HRID 372642Notes

Reaction equation

HRID 372642 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([Cl:10])[N:5]=[C:4]([NH:11][CH:12]([CH3:14])[CH3:13])[N:3]=1.[CH2:15]([NH2:17])[CH3:16]>CC(C)=O>[Cl:10][C:6]1[C:7]([C:8]#[N:9])=[C:2]([NH:17][CH2:15][CH3:16])[N:3]=[C:4]([NH:11][CH:12]([CH3:14])[CH3:13])[N:5]=1

Participants

4

Reactant 2

HCID 6341EthylamineHCID 205102654,6-Dichloro-2-isopropylamino-5-pyrimidinecarbonitrile

Product 1

HCID 205102154-Chloro-6-ethylamino-2-isopropylamino-5-pyrimidinecarbonitrile

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A stirred solution of 3.5 grams of 4,6-dichloro-2-isopropylamino-5-pyrimidinecarbonitrile in 100 ml of acetone was cooled to between 0° and -5°; a solution of 2.1 grams of aqueous 70% ethylamine in 25 ml of acetone was added dropwise. Upon complete addition, the reaction mixture was warmed to room temperature and stirred for 18 hours. The acetone was removed under reduced pressure, and 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 methylcyclohexane to give 3.1 grams of 4-chloro-6-ethylamino-2-isopropylamino-5-pyrimidinecarbonitrile; mp, 144°-146°.

Workup

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

Sources & evidence

ORD record
ord-56808d51d50e4ea6b902d37b407e4b43
Source dataset
uspto-grants-1978_05
Patent number
US04092150

Reaction notes

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