Sodium Hydroxide → 4,6-Dichloro-2-(1-cyano-1-methylethylamino)-5-pyrimidinecarbonitrile

HRID 1757888Notes

Reaction equation

HRID 1757888 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.[NH2:12][C:13]([CH3:17])([CH3:16])[C:14]#[N:15].[OH-].[Na+]>CC(C)=O.O>[Cl:11][C:4]1[C:5]([C:9]#[N:10])=[C:6]([Cl:8])[N:7]=[C:2]([NH:12][C:13]([C:14]#[N:15])([CH3:17])[CH3:16])[N:3]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 880222-Amino-2-methylpropionitrileHCID 2509452,4,6-Trichloro-5-cyanopyrimidine

Product 1

HCID 537123174,6-Dichloro-2-(1-cyano-1-methylethylamino)-5-pyrimidinecarbonitrileYield 40.7%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A stirred solution of 6.3 grams of 2,4,6-trichloro-5-pyrimidinecarbonitrile in 25 ml of acetone was cooled to -10°, and 2.5 grams of 2-amino-2-methylpropionitrile was added. With the reaction mixture at -10°, a solution of 1.3 grams of sodium hydroxide in 3.5 ml of water was added dropwise. Upon complete addition, the reaction mixture was stirred at -10° for 30 minutes. The acetone was removed under reduced pressure; the residue was extracted with diethyl ether, and the extract was separated and dried over magnesium sulfate. The extract was filtered, and the filtrate was evaporated under reduced pressure, yielding a residue. The residue was recrystallized from methylcyclohexane to give 3.1 grams of 4,6-dichloro-2-(1-cyano-1-methylethylamino)-5-pyrimidinecarbonitrile; mp, 154°-158°.

Workup

  1. additionUpon complete addition
  2. customThe acetone was removed under reduced pressure
  3. extractionthe residue was extracted with diethyl ether
  4. customthe extract was separated
  5. dry with materialdried over magnesium sulfate
  6. filtrationThe extract was filtered
  7. customthe filtrate was evaporated under reduced pressure
  8. customyielding a residue
  9. customThe residue was recrystallized from methylcyclohexane

Sources & evidence

ORD record
ord-ab6e5b595ff94bca80b70fde3467d008
Source dataset
uspto-grants-1983_02
Patent number
USRE031136

Reaction notes

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