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

HRID 372645Notes

Reaction equation

HRID 372645 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([Cl:10])[N:5]=[C:4]([NH:11][CH2:12][CH3:13])[N:3]=1.[CH:14]([NH2:17])([CH3:16])[CH3:15]>CC(C)=O>[Cl:10][C:6]1[C:7]([C:8]#[N:9])=[C:2]([NH:17][CH:14]([CH3:16])[CH3:15])[N:3]=[C:4]([NH:11][CH2:12][CH3:13])[N:5]=1

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 205102564,6-Dichloro-2-ethylamino-5-pyrimidinecarbonitrile

Product 1

HCID 205102214-Chloro-2-ethylamino-6-isopropylamino-5-pyrimidinecarbonitrileYield 94.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a stirred solution of 6.5 grams of 4,6-dichloro-2-ethylamino-5-pyrimidinecarbonitrile in 100 ml of acetone was added dropwise 7.4 grams of isopropylamine in 30 ml of acetone. Upon complete addition, the reaction mixture was stirred at room temperature for 16 hours. The acetone was removed by evaporation under reduced pressure, and the solid residue was washed with water. The resultant solid was collected by filtration to give 6.8 grams of 4-chloro-2-ethylamino-6-isopropylamino-5-pyrimidinecarbonitrile; mp 160°-165°. Recrystallization from a mixture of benzene and methylcyclohexane gave purified product; mp, 163°-165°.

Workup

  1. additionUpon complete addition
  2. customThe acetone was removed by evaporation under reduced pressure
  3. washthe solid residue was washed with water
  4. filtrationThe resultant solid was collected by filtration

Sources & evidence

ORD record
ord-fc23c464532649029808b723802f6192
Source dataset
uspto-grants-1978_05
Patent number
US04092150

Reaction notes

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