Diisopropylethylamine → (5-Bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-[3-(tert-butyl-dimethyl-silanyloxymethyl)-4-morpholin-4-yl-phenyl]-amine

HRID 605924Notes

Reaction equation

HRID 605924 reaction equation
[Br:1][C:2]1[N:7]2[N:8]=[CH:9][N:10]=[C:6]2[C:5](Br)=[N:4][CH:3]=1.[C:12]([SiH2:16][O:17][C:18]([CH3:33])([CH3:32])[C:19]1[CH:20]=[C:21]([NH2:31])[CH:22]=[CH:23][C:24]=1[N:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1)([CH3:15])([CH3:14])[CH3:13].C(N(C(C)C)C(C)C)C>CC(O)C>[Br:1][C:2]1[N:7]2[N:8]=[CH:9][N:10]=[C:6]2[C:5]([NH:31][C:21]2[CH:22]=[CH:23][C:24]([N:25]3[CH2:26][CH2:27][O:28][CH2:29][CH2:30]3)=[C:19]([C:18]([CH3:33])([CH3:32])[O:17][SiH2:16][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:20]=2)=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 497580225,8-Dibromo-(1,2,4)triazolo(1,5-a)pyrazineHCID 1373286683-(Tert-butyl-dimethyl-silanyloxymethyl)-4-morpholin-4-yl-phenylamine

Product 1

HCID 131727350(5-Bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-[3-(tert-butyl-dimethyl-silanyloxymethyl)-4-morpholin-4-yl-phenyl]-amineYield 46%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 5,8-dibromo-[1,2,4]triazolo[1,5-a]pyrazine (0.391 g, 1.41 mmol), 3-(tert-butyl-dimethyl-silanyloxymethyl)-4-morpholin-4-yl-phenylamine (0.5 g, 1.55 mmol) and N-ethyldiisopropyl-amine (0.27 mL, 1.55 mmol) is heated at 90° C. in 2-propanol (10 mL) for 8 hours. The reaction mixture is evaporated to dryness and the residue partitioned between dichloromethane and water. The aqueous phase is extracted twice with dichloromethane. The organic layers are combined, washed with brine, dried over MgSO4, filtrated and concentrated in vacuo to afford the title compound (335 mg, 46%).

Workup

  1. customThe reaction mixture is evaporated to dryness
  2. customthe residue partitioned between dichloromethane and water
  3. extractionThe aqueous phase is extracted twice with dichloromethane
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltrated
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e15a052ce3e84ef982dfb0c051a482fc
Source dataset
uspto-grants-2011_03
Patent number
US07915256B2

Reaction notes

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