Diisopropylethylamine → HCID 117779043, compound

HRID 1527125Notes

Reaction equation

HRID 1527125 reaction equation
[NH2:1][CH:2]([CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)[CH3:3].[Br:17][C:18]1[C:19](Cl)=[N:20][C:21]([Cl:24])=[N:22][CH:23]=1.C(N(C(C)C)C(C)C)C>C(O)C>[Br:17][C:18]1[C:19]([NH:1][CH:2]([CH:4]2[CH2:5][CH2:6][N:7]([C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])[CH2:8][CH2:9]2)[CH3:3])=[N:20][C:21]([Cl:24])=[N:22][CH:23]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2899735-Bromo-2,4-dichloropyrimidineHCID 22647295tert-Butyl 4-(1-aminoethyl)piperidine-1-carboxylate

Product 1

HCID 117779043HCID 117779043, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To the solution of tert-butyl 4-(1-aminoethyl)piperidine-1-carboxylate (5 g, 21.9 mmol) in ethanol (50 ml) were added 5-bromo-2,4-dichloropyrimidine (5.97 g, 26.3 mmol), and N-ethyl-N-isopropylpropan-2-amine (8.48 g, 65.7 mmol). The resulting mixture was stirred at room temperature overnight. The reaction mixture was concentrated in vacuum, and the crude product was added to water (100 ml). The aqueous layer was extracted with ethyl acetate (50 mL×4) and organic layer was dried over sodium sulfate and concentrated to give crude product tert-butyl 4-(1-((5-bromo-2-chloropyrimidin-4-yl)amino)ethyl)piperidine-1-carboxylate (7 g, yield: 97.2%) as a yellow oil. LRMS (M+H+) m/z: calcd 418. found 419.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuum
  2. additionthe crude product was added to water (100 ml)
  3. extractionThe aqueous layer was extracted with ethyl acetate (50 mL×4) and organic layer
  4. dry with materialwas dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fbe2bf59430f4f3f9f8837caea789d77
Source dataset
uspto-grants-2015_07
Patent number
US09085583B2

Reaction notes

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