Diisopropylethylamine → HCID 73507292, compound

HRID 1478594Notes

Reaction equation

HRID 1478594 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[N:12]=[C:11]3[N:13]([CH2:16][CH:17]4[CH2:22][CH2:21][CH2:20][NH:19][CH2:18]4)[N:14]=[N:15][C:10]3=[N:9][CH:8]=2)[CH:4]=[N:3]1.[Br:23][C:24]1[CH:25]=[N:26][C:27](Cl)=[N:28][CH:29]=1.CCN(C(C)C)C(C)C>CCO>[Br:23][C:24]1[CH:25]=[N:26][C:27]([N:19]2[CH2:20][CH2:21][CH2:22][CH:17]([CH2:16][N:13]3[C:11]4=[N:12][C:7]([C:5]5[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=5)=[CH:8][N:9]=[C:10]4[N:15]=[N:14]3)[CH2:18]2)=[N:28][CH:29]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 6066655-Bromo-2-chloropyrimidineHCID 118364825HCID 118364825, compound

Product 1

HCID 73507292HCID 73507292, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

6-(1-methyl-1H-pyrazol-4-yl)-1-(piperidin-3-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazine (0.26 g, 0.89 mmol) was dissolved in EtOH (15 ml), and then 5-bromo-2-chloropyrimidine (0.33 g, 1.33 mmol) and DIPEA (0.77 ml, 4.43 mmol) were added, followed by stirring at 50° C. overnight. After the completion of the reaction, the reaction mixture was extracted with H2O, EA, and brine, followed by drying (Na2SO4), filtration, and concentration under reduced pressure, and the residue was purified by column chromatography (EA:Hex=1:1), to give (1-((1-(5-bromopyrimidin-2-yl)piperidin-3-yl)methyl)-6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazine (0.28 g, 70%).

Workup

  1. customAfter the completion of the reaction
  2. extractionthe reaction mixture was extracted with H2O, EA, and brine
  3. customby drying
  4. filtration(Na2SO4), filtration, and concentration under reduced pressure
  5. customthe residue was purified by column chromatography (EA:Hex=1:1)

Sources & evidence

ORD record
ord-51dfd0eeb5aa4d8688343c72f3d0974e
Source dataset
uspto-grants-2016_08
Patent number
US09403831B2

Reaction notes

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