Triethylamine → HCID 178503436, compound

HRID 1809695Notes

Reaction equation

HRID 1809695 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.[NH2:19][CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]1.C(N(CC)CC)C>CC(O)C>[C:31]([O:30][C:28]([N:25]1[CH2:24][CH2:23][N:22]([CH2:21][CH2:20][NH:19][C:2]2[N:7]=[C:6]3[NH:8][N:9]=[C:10]([C:11]4[CH:16]=[CH:15][N:14]=[C:13]([S:17][CH3:18])[N:12]=4)[C:5]3=[CH:4][N:3]=2)[CH2:27][CH2:26]1)=[O:29])([CH3:34])([CH3:33])[CH3:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1514400tert-Butyl 4-(2-aminoethyl)piperazine-1-carboxylateHCID 178503430HCID 178503430, compound

Product 1

HCID 178503436HCID 178503436, compound

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) (500 mg, 1.79 mmol) in 2-propanol (40 mL) was added tert-butyl 4-(2-aminoethyl)piperazine-1-carboxylate (613 mg, 1.97 mmol) followed by triethylamine (200 mg, 1.98 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 4-{2-[3-(2-methylsulfanyl-pyrimidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino]-ethyl}-piperazine-1-carboxylic acid tert-butyl ester. (Yield 600 mg, crude).

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-a1d511ab40204b4b91a828d9de70afc6
Source dataset
uspto-grants-2013_01
Patent number
US08362023B2

Reaction notes

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