Water → 4-Chloro-2-(1-cyano-1-methylethylamino)-6-ethylamino-5-pyrimidinecarbonitrile

HRID 372646Notes

Reaction equation

HRID 372646 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([Cl:10])[N:5]=[C:4]([NH:11][C:12]([C:15]#[N:16])([CH3:14])[CH3:13])[N:3]=1.[CH2:17]([NH2:19])[CH3:18].O>CC(C)=O>[Cl:10][C:6]1[C:7]([C:8]#[N:9])=[C:2]([NH:19][CH2:17][CH3:18])[N:3]=[C:4]([NH:11][C:12]([C:15]#[N:16])([CH3:14])[CH3:13])[N:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6341EthylamineHCID 537123174,6-Dichloro-2-(1-cyano-1-methylethylamino)-5-pyrimidinecarbonitrile

Product 1

HCID 538166454-Chloro-2-(1-cyano-1-methylethylamino)-6-ethylamino-5-pyrimidinecarbonitrile

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A stirred solution of 5.1 grams of 4,6-dichloro-2-(1-cyano-1-methylethylamino)-5-pyrimidinecarbonitrile in 50 ml of acetone was cooled to 0° to -5°, and 2.8 grams of an aqueous solution of 70% ethylamine in 40 ml of acetone was added dropwise. The temperature of the reaction mixture was maintained at 0° to -5° throughout the addition, then during 2 hours following complete addition. The reaction mixture was warmed to room temperature where it was stirred for 1 hour. Water was added to the reaction mixture, which caused precipitation of a solid. The solid was collected by filtration and recrystallized from a mixture of benzene and methylcyclohexane to give 3.3 grams of 4-chloro-2-(1-cyano-1-methylethylamino)-6-ethylamino-5-pyrimidinecarbonitrile; mp, 157°-160°.

Workup

  1. temperatureThe temperature of the reaction mixture was maintained at 0° to -5° throughout the addition
  2. additionaddition
  3. customprecipitation of a solid
  4. filtrationThe solid was collected by filtration
  5. customrecrystallized from a mixture of benzene and methylcyclohexane

Sources & evidence

ORD record
ord-62b82a27ad60439abc8fbbdcfa9aa68a
Source dataset
uspto-grants-1978_05
Patent number
US04092150

Reaction notes

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