Cyclopropylamine → 4-Chloro-6-cyclopropylamino-2-diethylamino-5-pyrimidinecarbonitrile

HRID 372651Notes

Reaction equation

HRID 372651 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([Cl:10])[N:5]=[C:4]([N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])[N:3]=1.[CH:16]1([NH2:19])[CH2:18][CH2:17]1>CC(C)=O>[Cl:10][C:6]1[C:7]([C:8]#[N:9])=[C:2]([NH:19][CH:16]2[CH2:18][CH2:17]2)[N:3]=[C:4]([N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])[N:5]=1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 205101864,6-Dichloro-2-diethylamino-5-pyrimidinecarbonitrile

Product 1

HCID 205102034-Chloro-6-cyclopropylamino-2-diethylamino-5-pyrimidinecarbonitrileYield 33.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a stirred solution of 6.9 grams of 4,6-dichloro-2-diethylamino-5-pyrimidinecarbonitrile in 80 ml of acetone was added dropwise 3.2 grams of cyclopropylamine in 20 ml of acetone. The reaction mixture stood for 16 hours; then the acetone was removed by evaporation under reduced pressure. The residue was washed with water, and the resultant solid was collected. The solid was washed several times with water, then dried, to give 6.5 grams of crude product; mp, 100°-105°. The crude product was recrystallized from petroleum ether to give 2.5 grams of 4-chloro-6-cyclopropylamino-2-diethylamino-5-pyrimidinecarbonitrile; mp, 120°-122°.

Workup

  1. customthen the acetone was removed by evaporation under reduced pressure
  2. washThe residue was washed with water
  3. customthe resultant solid was collected
  4. washThe solid was washed several times with water
  5. customdried
  6. customto give 6.5 grams of crude product
  7. custommp, 100°-105°
  8. customThe crude product was recrystallized from petroleum ether

Sources & evidence

ORD record
ord-689af0038fbe4c9ba0e44e49b909ce02
Source dataset
uspto-grants-1978_05
Patent number
US04092150

Reaction notes

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