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

HRID 1809683Notes

Reaction equation

HRID 1809683 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.[O:19]1[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][NH2:27])[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:27][CH2:26][CH2:25][N:22]4[CH2:23][CH2:24][O:19][CH2:20][CH2:21]4)=[N:3][CH:4]=3)[NH:8][N:9]=2)[CH:16]=[CH:15][N:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 4082852-MorpholinoethylamineHCID 178503430HCID 178503430, compound

Product 1

HCID 178503437[3-(2-methylsulfanyl-pyrimidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-(2-morpholin-4-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) (2 g, 7.19 mmol) in 2-propanol (100 mL) was added 2-morpholinoethanamine (1.0 g, 7.9 mmol) followed by triethylamine (800 mg, 7.9 mmol). The reaction mixture was stirred with heating at reflux for 6 hours. The solvent was then removed under reduced pressure. The residue was washed with 2-propanol and water to afford [3-(2-methylsulfanyl-pyrimidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-(2-morpholin-4-yl-ethyl)-amine. (Yield 2.1 g, 80%).

Workup

  1. temperaturewith heating
  2. temperatureat reflux for 6 hours
  3. customThe solvent was then removed under reduced pressure
  4. washThe residue was washed with 2-propanol and water

Sources & evidence

ORD record
ord-c88c7cb92ce0483a8e564d7b413ace0a
Source dataset
uspto-grants-2013_01
Patent number
US08362023B2

Reaction notes

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