Potassium Carbonate → HCID 135886513, compound

HRID 2424825Notes

Reaction equation

HRID 2424825 reaction equation
Cl.[CH2:2]([C@@H:4]1[CH2:8][NH:7][CH2:6][C@H:5]1[C:9]1[NH:10][C:11](=[O:24])[C:12]2[CH:17]=[N:16][N:15]([CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[C:13]=2[N:14]=1)[CH3:3].C(=O)([O-])[O-].[K+].[K+].Br.Br[CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=1>C(#N)C>[CH2:2]([C@@H:4]1[CH2:8][N:7]([CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=2)[CH2:6][C@H:5]1[C:9]1[NH:10][C:11](=[O:24])[C:12]2[CH:17]=[N:16][N:15]([CH:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)[C:13]=2[N:14]=1)[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27347202-(Bromomethyl)pyridine hydrobromideHCID 1363442016-[(3S,4S)-4-ethylpyrrolidin-3-yl]-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one hydrogen chloride

Product 1

HCID 135886513HCID 135886513, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 6-[(3S,4S)-4-ethylpyrrolidin-3-yl]-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one hydrogen chloride (51 mg) in acetonitrile (1 mL) was added potassium carbonate (88 mg) and 2-(bromomethyl)pyridine hydrogen bromide (40 mg) and the reaction mixture was heated at reflux for 72 h in a sealed vial. The reaction mixture was concentrated onto silica and purified via CombiFlash flash chromatography to provide the title compound. 400 MHz 1H NMR (CDCl3) δ 11.50 (brs, 1H), 8.63 (dd, J=1.7, 0.83, Hz, 1H), 8.02 (s, 1H), 7.70-7.67 (m, 1H), 7.40 (d, J=7.9 Hz, 1H), 7.20-7.16 (m, 1H), 4.79-4.77 (m, 1H), 4.12-4.02 (m, 3H), 3.75-3.72 (m, 1H), 3.61-3.53 (m, 2H), 3.39 (t, J=7.9 Hz, 1H), 3.07 (d, J=9.9 Hz, 1H), 2.92-2.90 (m, 1H), 2.37-2.12 (m, 4H), 1.91-1.83 (m, 2H), 1.65-1.60 (m, 1H), 1.54-1.49 (m, 1H), 0.94 (t, J=7.1 Hz, 3H). MS: (M+H m/z 409.1).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 72 h in a sealed vial
  3. concentrationThe reaction mixture was concentrated onto silica
  4. custompurified via CombiFlash flash chromatography

Sources & evidence

ORD record
ord-9d138aea5a874b4fba7b6a4a9bc0461c
Source dataset
uspto-grants-2011_06
Patent number
US07964607B2

Reaction notes

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