Diisopropylethylamine → HCID 10426913, compound

HRID 2216984Notes

Reaction equation

HRID 2216984 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([CH:9](Br)[CH3:10])=[CH:4][N:3]=1.C(N(CC)C(C)C)(C)C.Cl.[Cl:22][C:23]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:24]=1[NH2:25]>C(OCC)(=O)C>[Cl:22][C:23]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:24]=1[NH:25][CH:9]([C:5]1[C:6]([Cl:8])=[N:7][C:2]([Cl:1])=[N:3][CH:4]=1)[CH3:10]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27239002-Chloro-5-methoxyanilinium chlorideHCID 21908975(+/-)-2,4-Dichloro-5-(1-bromoethyl)-pyrimidine

Product 1

HCID 10426913HCID 10426913, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

(±)-2,4-Dichloro-5-(1-bromoethyl)-pyrimidine (0.20 g; 0.79 mmol) (from Example 1c supra), N,N-diisopropylethylamine (0.40 mL; 2.27 mmol) (Aldrich) and 2-chloro-5-methoxyaniline hydrochloride (0.15 g; 0.77 mmol) (Aldrich) were combined (neat) and heated in an oil bath at 90° C. for 16 hours. Upon cooling, the mixture was taken up in ethyl acetate and washed with water and then brine. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. Purification by flash chromatography (Biotage 40M; 5:95 to 15:85 ethyl acetate-hexanes gradient) gave (±)-(2-chloro-5-methoxy-phenyl)-[1-(2,4-dichloro-pyrimidin-5-yl)-ethyl]-amine. (Yield 0.12 g; 45.9%).

Workup

  1. temperatureUpon cooling
  2. washwashed with water
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography (Biotage 40M; 5:95 to 15:85 ethyl acetate-hexanes gradient)

Sources & evidence

ORD record
ord-1fcc243e640a493ab9a9bf7469744992
Source dataset
uspto-grants-2006_09
Patent number
US07112676B2

Reaction notes

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