Diethylamine → 4-Chloro-2,6-bis(diethylamino)-5-pyrimidinecarbonitrile

HRID 372643Notes

Reaction equation

HRID 372643 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[C:5]([C:9]#[N:10])=[C:4](Cl)[N:3]=1.[CH2:12]([NH:14][CH2:15][CH3:16])[CH3:13]>C(OCC)C>[Cl:8][C:6]1[C:5]([C:9]#[N:10])=[C:4]([N:14]([CH2:15][CH3:16])[CH2:12][CH3:13])[N:3]=[C:2]([N:14]([CH2:15][CH3:16])[CH2:12][CH3:13])[N:7]=1

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 2509452,4,6-Trichloro-5-cyanopyrimidine

Product 1

HCID 205101744-Chloro-2,6-bis(diethylamino)-5-pyrimidinecarbonitrile

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred solution of 6.3 grams of 2,4,6-trichloro-5-pyrimidinecarbonitrile in 150 ml of diethyl ether at 10° was added dropwise 8.8 grams of diethylamine in 150 ml of diethyl ether. Upon complete addition, the reaction mixture was allowed to warm to room temperature, where it was stirred for 16 hours. The reaction mixture was heated under reflux for 1 hour, then cooled to room temperature. The reaction mixture was washed with water, and the diethyl ether layer was separated. The aqueous layer was washed with diethyl ether. The ether layers were combined 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 petroleum ether to give crude 4-chloro-2,6-bis(diethylamino)-5-pyrimidinecarbonitrile. This crude material was dissolved in diethyl ether, and 4.4 grams of diethylamine was added.

Workup

  1. additionUpon complete addition
  2. temperatureThe reaction mixture was heated
  3. temperatureunder reflux for 1 hour
  4. temperaturecooled to room temperature
  5. washThe reaction mixture was washed with water
  6. customthe diethyl ether layer was separated
  7. washThe aqueous layer was washed with diethyl ether
  8. dry with materialdried over magnesium sulfate
  9. filtrationThe mixture was filtered
  10. customthe filtrate was evaporated under reduced pressure to a residue
  11. customThe residue was recrystallized from petroleum ether

Sources & evidence

ORD record
ord-462e0eacb38c4b88bc751ef552edc781
Source dataset
uspto-grants-1978_05
Patent number
US04092150

Reaction notes

Loading…