Triethylamine → [3-(3-bromo-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-(2-morpholin-4-yl-ethyl)-amine

HRID 1809708Notes

Reaction equation

HRID 1809708 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]3[C:11](=[N:12][C:13](Cl)=[N:14][CH:15]=3)[NH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.CCN(CC)CC.Cl[CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31].[O:34]1[CH2:39][CH2:38][N:37]([CH2:40][CH2:41][NH2:42])[CH2:36][CH2:35]1>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]3[C:11](=[N:12][C:13]([NH:42][CH2:41][CH2:40][N:37]4[CH2:38][CH2:39][O:34][CH2:35][CH2:36]4)=[N:14][CH:15]=3)[N:10]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 4082852-MorpholinoethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 178478326HCID 178478326, compound

Product 1

HCID 68109320[3-(3-bromo-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-(2-morpholin-4-yl-ethyl)-amine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(3-bromo-phenyl)-6-chloro-1H-pyrazolo[3,4-d]pyrimidine (from Example 38 supra) (3.0 g, 9.7 mmol), Et3N (5.4 mL, 38.8 mmol) in DMF (50 mL), (2-(chloromethoxy)-ethyl)trimethylsilane (SEM-Cl, 2.0 mL, 11.6 mmol) was added in one portion. The resultant mixture was stirred for 30 minutes at room temperature. To this solution, 2-morpholino-ethanamine (1.51 g, 11.6 mmol) was added. The resulting mixture was stirred for one hour at room temperature. The reaction was poured into water (200 mL), extracted with EtOAc (3×200 mL), dried over Na2SO4, filtered and concentrated. The crude product was purified by chromatography (silica gel, 200-300 mesh, EtOAc) to give [3-(3-bromo-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-(2-morpholin-4-yl-ethyl)-amine as yellow oil. (Yield 1.7 g, 32.7%).

Workup

  1. extractionextracted with EtOAc (3×200 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by chromatography (silica gel, 200-300 mesh, EtOAc)

Sources & evidence

ORD record
ord-8d48cb8cc9704bea9987de46fb381d07
Source dataset
uspto-grants-2013_01
Patent number
US08362023B2

Reaction notes

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