Diethylamine → 4-Chloro-6-diethylamino-2-isopropylamino-5-pyrimidinecarbonitrile

HRID 1757896Notes

Reaction equation

HRID 1757896 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]([NH:17][CH2:18][CH3:19])[CH3:16]>C(OCC)C>[Cl:10][C:6]1[C:7]([C:8]#[N:9])=[C:2]([N:17]([CH2:18][CH3:19])[CH2:15][CH3:16])[N:3]=[C:4]([NH:11][CH:12]([CH3:14])[CH3:13])[N:5]=1

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 205102654,6-Dichloro-2-isopropylamino-5-pyrimidinecarbonitrile

Product 1

HCID 205102144-Chloro-6-diethylamino-2-isopropylamino-5-pyrimidinecarbonitrileYield 50.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 4.3 grams of 4,6-dichloro-2-isopropylamino-5-pyrimidinecarbonitrile in 125 ml of diethyl ether was added dropwise 2.6 grams of diethylamine. Upon complete addition, the reaction mixture was stirred at room temperature for 1.5 hours. The reaction mixture was washed with water. The diethyl ether layer was separated and dried over magnesium sulfate. The mixture was filtered, and the filtrate was evaporated under reduced pressure to a residue. The residue was recrystallized from methylcyclohexane to give 2.5 grams of 4-chloro-6-diethylamino-2-isopropylamino-5-pyrimidinecarbonitrile; mp, 74°-76°.

Workup

  1. additionUpon complete addition
  2. washThe reaction mixture was washed with water
  3. customThe diethyl ether layer was separated
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe mixture was filtered
  6. customthe filtrate was evaporated under reduced pressure to a residue
  7. customThe residue was recrystallized from methylcyclohexane

Sources & evidence

ORD record
ord-8dd785c8eeac45afbd6744b874eb1cc5
Source dataset
uspto-grants-1983_02
Patent number
USRE031136

Reaction notes

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