Diisopropylethylamine → HCID 73507291, compound

HRID 1478559Notes

Reaction equation

HRID 1478559 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[N:12]=[C:11]3[N:13]([CH2:16][C@H:17]4[O:22][CH2:21][CH2:20][N:19]([C:23](OC(C)(C)C)=O)[CH2:18]4)[N:14]=[N:15][C:10]3=[N:9][CH:8]=2)[CH:4]=[N:3]1.[Br:30][C:31]1[CH:32]=[N:33]C(Cl)=[N:35][CH:36]=1.CCN(C(C)C)C(C)C>CCO>[Br:30][C:31]1[CH:36]=[N:35][C:23]([N:19]2[CH2:20][CH2:21][O:22][C@H: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:33][CH:32]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 6066655-Bromo-2-chloropyrimidineHCID 118364809(S)-tert-butyl 2-((6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)morpholine-4-carboxylate

Product 1

HCID 73507291HCID 73507291, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(S)-tert-butyl 2-((6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)morpholine-4-carboxylate (16.4 g, 54.69 mmol) was dissolved in EtOH (500 ml), and 5-bromo-2-chloropyrimidine (12.7 g, 65.62 mmol) and DIPEA (47.6 g, 273.45 mmol) were added, followed by 50° C. for 9 hours. After the completion of the reaction, the reaction mixture was recrystallized with EtOH to give (S)-4-(5-bromopyrimidin-2-yl)-2-((6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)morpholine (18.7 g, 75%).

Workup

  1. customAfter the completion of the reaction
  2. customthe reaction mixture was recrystallized with EtOH

Sources & evidence

ORD record
ord-c6d5cb4331614d75ad13997e574c3524
Source dataset
uspto-grants-2016_08
Patent number
US09403831B2

Reaction notes

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