Hydrochloric Acid → N-(4-Diethylamino-phenyl)-pyrimidine-4,6-diamine

HRID 1038669Notes

Reaction equation

HRID 1038669 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.[NH2:9][C:10]1[CH:20]=[CH:19][C:13]([N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])=[CH:12][CH:11]=1.Cl.C([O-])([O-])=O.[K+].[K+]>C(OCC)(=O)C.CC(O)C>[CH2:17]([N:14]([CH2:15][CH3:16])[C:13]1[CH:19]=[CH:20][C:10]([NH:9][C:2]2[CH:3]=[C:4]([NH2:8])[N:5]=[CH:6][N:7]=2)=[CH:11][CH:12]=1)[CH3:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7120N,N-Diethyl-p-phenylenediamineHCID 11430Potassium CarbonateHCID 2380124-Amino-6-chloropyrimidine

Product 1

HCID 66669959N-(4-Diethylamino-phenyl)-pyrimidine-4,6-diamine

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 6-chloro-pyrimidin-4-ylamine (0.65 g, 5 mmol), 4-amino-N,N-diethylaniline (0.82 mL, 5 mmol), 2-propanol (5 mL) and HCl conc. (0.225 mL, ˜2.5 mmol) is shaken for 36 h at 90° C. After cooling to room temperature, the reaction mixture is distributed between half-saturated K2CO3-solution and ethyl acetate. The precipitate thus formed is filtered off, washed with H2O and ethyl acetate and dried in vacuo to afford the title compound. Greyish solid, HPLC: tR=2.37 min (gradient F), ESI-MS: 258.3 [MH]+.

Workup

  1. temperatureAfter cooling to room temperature
  2. customThe precipitate thus formed
  3. filtrationis filtered off
  4. washwashed with H2O and ethyl acetate
  5. customdried in vacuo

Sources & evidence

ORD record
ord-803fc22fd51e458a93255b3779eee617
Source dataset
uspto-grants-2013_10
Patent number
US08552002B2

Reaction notes

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