1-Pyrrolidineethanamine → [3-(2-methylsulfanyl-pyrimidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-(2-pyrrolidin-1-yl-ethyl)-amine

HRID 1809688Notes

Reaction equation

HRID 1809688 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.[N:19]1([CH2:24][CH2:25][NH2:26])[CH2:23][CH2:22][CH2:21][CH2:20]1.C(N(CC)CC)C>CC(O)C>[CH3:18][S:17][C:13]1[N:12]=[C:11]([C:10]2[C:5]3[C:6](=[N:7][C:2]([NH:26][CH2:25][CH2:24][N:19]4[CH2:23][CH2:22][CH2:21][CH2:20]4)=[N:3][CH:4]=3)[NH:8][N:9]=2)[CH:16]=[CH:15][N:14]=1

Participants

5

Reactant 3

HCID 13441-PyrrolidineethanamineHCID 8471TriethylamineHCID 178503430HCID 178503430, compound

Product 1

HCID 178503434[3-(2-methylsulfanyl-pyrimidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-(2-pyrrolidin-1-yl-ethyl)-amine

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, 1.8 mmol) in 2-propanol (40 mL) was added 2-(pyrrolidin-1-yl)ethanamine (226 mg, 2.0 mmol) followed by triethylamine (200 mg, 2.0 mmol). The reaction mixture was stirred at reflux for 15 hours and the solvent was 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 [3-(2-methylsulfanyl-pyrimidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-(2-pyrrolidin-1-yl-ethyl)-amine. (Yield 500 mg, 78.1%).

Workup

  1. temperatureat reflux for 15 hours
  2. customthe solvent was 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-9acd207926a94f569d514d2bd026d9ec
Source dataset
uspto-grants-2013_01
Patent number
US08362023B2

Reaction notes

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