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 1783943Notes

Reaction equation

HRID 1783943 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-c3d56357835e4c608cff369d74c8512d
Source dataset
uspto-grants-2009_03
Patent number
US07501411B2

Reaction notes

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