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

HRID 372638Notes

Reaction equation

HRID 372638 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.[CH:12]([NH2:15])([CH3:14])[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]([NH:15][CH:12]([CH3:14])[CH3:13])[N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6363IsopropylamineHCID 2509452,4,6-Trichloro-5-cyanopyrimidine

Product 1

HCID 205102654,6-Dichloro-2-isopropylamino-5-pyrimidinecarbonitrileYield 51.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A stirred solution of 4.2 grams of 2,4,6-trichloro-5-pyrimidinecarbonitrile in 100 ml of diethyl ether was cooled to between -5° and -10°, and a solution of 2.4 grams of isopropylamine in 100 ml of diethyl ether was added dropwise. Upon complete addition, water was added to the reaction mixture, and the ether layer was separated. The ethereal layer was dried over magnesium sulfate and filtered. The filtrate was evaporated to dryness under reduced pressure. The residue was recrystallized from methylcyclohexane to give 2.4 grams of 4,6-dichloro-2-isopropylamino-5-pyrimidinecarbonitrile; mp, 179°-181°.

Workup

  1. additionwas added to the reaction mixture
  2. customthe ether layer was separated
  3. dry with materialThe ethereal layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness under reduced pressure
  6. customThe residue was recrystallized from methylcyclohexane

Sources & evidence

ORD record
ord-35d9fab74f5c4c15b46e7358f66413e6
Source dataset
uspto-grants-1978_05
Patent number
US04092150

Reaction notes

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