Hydrochloric Acid → HCID 66669910, compound

HRID 1038671Notes

Reaction equation

HRID 1038671 reaction equation
[CH3:1][N:2]([CH3:10])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([NH2:9])[CH:4]=1.Cl[C:12]1[N:17]=[CH:16][N:15]=[C:14]([NH2:18])[CH:13]=1.Cl.C([O-])([O-])=O.[Na+].[Na+]>C(OCC)(=O)C.CC(O)C>[CH3:1][N:2]([CH3:10])[C:3]1[CH:4]=[C:5]([NH:9][C:12]2[CH:13]=[C:14]([NH2:18])[N:15]=[CH:16][N:17]=2)[CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 76084N,N-dimethyl-m-phenylenediamineHCID 2380124-Amino-6-chloropyrimidine

Product 1

HCID 66669910HCID 66669910, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of N,N-dimethyl-m-phenylenediamine (1.36 g, 10 mmol), 6-chloro-pyrimidin-4-ylamine (1.30 g, 10 mmol), 2-propanol (10 mL) and HCl conc. (0.45 mL, ˜5 mmol) is shaken for 16 h at 90° C. After cooling to room temperature, the reaction mixture is distributed between half-concentrated Na2CO3 solution and ethyl acetate. The organic layer is dried over Na2SO4, evaporated, and the residue purified by flash chromatography (ethyl acetate/CH3OH). The combined pure fractions are evaporated to afford the title compound. Beige solid, HPLC: tR=1.53 min (gradient F), ESI-MS: 230.3 [MH]+.

Workup

  1. temperatureAfter cooling to room temperature
  2. dry with materialThe organic layer is dried over Na2SO4
  3. customevaporated
  4. customthe residue purified by flash chromatography (ethyl acetate/CH3OH)
  5. customThe combined pure fractions are evaporated

Sources & evidence

ORD record
ord-aa0bd0574f6d400985ea9543a024912c
Source dataset
uspto-grants-2013_10
Patent number
US08552002B2

Reaction notes

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