Potassium Carbonate → N,N-Diethyl-6-methyl-2-(4-pyridinyl)-4-pyrimidinamine

HRID 236678Notes

Reaction equation

HRID 236678 reaction equation
ClC1C=C(C)N=C(C2C=CN=CC=2)N=1.Cl.C(NCC)C.C(=O)([O-])[O-].[K+].[K+].Cl.Cl.[CH2:29]([N:31]([CH2:45][CH3:46])[C:32]1[CH:37]=[C:36]([CH3:38])[N:35]=[C:34]([C:39]2[CH:44]=[CH:43][N:42]=[CH:41][CH:40]=2)[N:33]=1)[CH3:30]>O.C(O)C>[CH2:45]([N:31]([CH2:29][CH3:30])[C:32]1[CH:37]=[C:36]([CH3:38])[N:35]=[C:34]([C:39]2[CH:44]=[CH:43][N:42]=[CH:41][CH:40]=2)[N:33]=1)[CH3:46]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 10197650Diethylammonium chlorideHCID 127647054-Chloro-6-methyl-2-(pyridin-4-yl)pyrimidineHCID 12764719N,N-diethyl-6-methyl-2-(4-pyridinyl)-4-pyrimidinamine dihydrochloride

Product 1

HCID 12764718N,N-Diethyl-6-methyl-2-(4-pyridinyl)-4-pyrimidinamine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture containing 8.2 g. of 4-chloro-6-methyl-2-(4-pyridinyl)pyrimidine, 8.7 g. of diethylamine hydrochloride, 100 ml. of ethanol, 6 g. of potassium carbonate and 10 ml. of water was refluxed with stirring for eight hours and then concentrated in vacuo to dryness. The residue was swirled in water and the solid collected. The solid was dissolved in boiling isopropyl alcohol, the hot solution treated with decolorizing charcoal and filtered, and the hot filtrate allowed to cool. The filtrate was then saturated with gaseous hydrogen chloride, ether was added to turbidity and the mixture was allowed to stand. The separated solid was collected and dried in vacuo at 80° C. to yield 7.4 g. of N,N-diethyl-6-methyl-2-(4-pyridinyl)-4-pyrimidinamine dihydrochloride, m.p. 205°-208° C.

Workup

  1. additionA mixture containing 8.2 g
  2. concentrationconcentrated in vacuo to dryness
  3. customthe solid collected
  4. dissolutionThe solid was dissolved
  5. additionthe hot solution treated with decolorizing charcoal
  6. filtrationfiltered
  7. temperatureto cool
  8. additionsaturated with gaseous hydrogen chloride, ether was added to turbidity
  9. customThe separated solid was collected
  10. customdried in vacuo at 80° C.
  11. customto yield 7.4 g

Sources & evidence

ORD record
ord-179b9f13f14640e5ba8919e1c2e7dc77
Source dataset
uspto-grants-1979_06
Patent number
USRE030024

Reaction notes

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