Water → 4,6-Dichloro-2-diethylamino-5-pyrimidinecarbonitrile

HRID 372639Notes

Reaction equation

HRID 372639 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[C:5]([C:9]#[N:10])=[C:4]([Cl:11])[N:3]=1.[CH2:12]([NH:14][CH2:15][CH3:16])[CH3:13].O>C(OCC)C>[Cl:11][C:4]1[C:5]([C:9]#[N:10])=[C:6]([Cl:8])[N:7]=[C:2]([N:14]([CH2:15][CH3:16])[CH2:12][CH3:13])[N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8021DiethylamineHCID 2509452,4,6-Trichloro-5-cyanopyrimidine

Product 1

HCID 205101864,6-Dichloro-2-diethylamino-5-pyrimidinecarbonitrileYield 51.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A stirred solution of 6.3 grams of 2,4,6-trichloro-5-pyrimidinecarbonitrile in 150 ml of diethyl ether was cooled to -10°, and a solution of 4.4 grams of diethylamine in 75 ml of diethyl ether was added dropwise. Upon complete addition, the reaction mixture was stirred at -10° for 1 hour. Water was added to the reaction mixture. 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 3.8 grams of 4,6-dichloro-2-diethylamino-5-pyrimidinecarbonitrile; mp, 125°-126°.

Workup

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

Sources & evidence

ORD record
ord-cb25011bd985431980af3dd66e701930
Source dataset
uspto-grants-1978_05
Patent number
US04092150

Reaction notes

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