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

HRID 1757897Notes

Reaction equation

HRID 1757897 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-3a2b5be0683a4f8caa4b9560de9a70cc
Source dataset
uspto-grants-1983_02
Patent number
USRE031136

Reaction notes

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