Triethylamine → HCID 178503438, compound

HRID 1809693Notes

Reaction equation

HRID 1809693 reaction equation
Cl[C:2]1[N:7]=[C:6]2[NH:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([S:17][CH3:18])[N:12]=3)[C:5]2=[CH:4][N:3]=1.[CH3:19][N:20]([CH3:24])[CH2:21][CH2:22][NH2:23].C(N(CC)CC)C>CC(O)C>[CH3:19][N:20]([CH3:24])[CH2:21][CH2:22][NH:23][C:2]1[N:7]=[C:6]2[NH:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([S:17][CH3:18])[N:12]=3)[C:5]2=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66053N,N-DimethylethylenediamineHCID 178503430HCID 178503430, compound

Product 1

HCID 178503438HCID 178503438, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 6-chloro-3-(2-methylsulfanyl-pyrimidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidine (from Example 7 supra) (400 mg, 1.43 mmol) in 2-propanol (40 mL) was added N, N-dimethylethane-1,2-diamine (139 mg, 1.58 mmol) followed by triethylamine (159 mg, 1.57 mmol). The reaction mixture was stirred at reflux for 15 hours and the solvent was then removed under reduced pressure. The residue was extracted with dichloromethane (3×30 mL), washed with water (5 mL), dried over anhydrous sodium sulfate, filtered, and concentrated to afford N,N-dimethyl-N′-[3-(2-methylsulfanyl-pyrimidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-ethane-1,2-diamine (Yield 356 mg, 75%).

Workup

  1. temperatureat reflux for 15 hours
  2. customthe solvent was then removed under reduced pressure
  3. extractionThe residue was extracted with dichloromethane (3×30 mL)
  4. washwashed with water (5 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-054f093b3b7b44ee84de12be77728e61
Source dataset
uspto-grants-2013_01
Patent number
US08362023B2

Reaction notes

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