Thionyl Chloride → 5-(chloromethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine

HRID 564522Notes

Reaction equation

HRID 564522 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]([N:7]1[C:11]2=[N:12][C:13]([CH2:25][CH3:26])=[C:14]([CH2:23]O)[C:15]([NH:16][CH:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[C:10]2[CH:9]=[N:8]1)[CH3:6]>>[Cl:3][CH2:23][C:14]1[C:13]([CH2:25][CH3:26])=[N:12][C:11]2[N:7]([CH2:5][CH3:6])[N:8]=[CH:9][C:10]=2[C:15]=1[NH:16][CH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 59683222[1,6-Diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methanol

Product 1

HCID 596832285-(chloromethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amineYield 60%

Procedure

To a solution of thionyl chloride (1.46 mL, 20.0 mmol) was added [1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methanol (0.609 g, 2.0 mmol) slowly. The mixture was stirred at room temperature for 30 min and then was concentrated on rotavap under vacuum. The residue was twice taken up in DCM (5 mL) and concentrated on rotavap to afford the title compound 0.386 g (60%). LC-MS m/z 319 (M+H)+ [molecular ion of the compound with methoxy from LC-MS solvent methanol where OMe substituted chloro group of the original product].

Workup

  1. concentrationwas concentrated on rotavap under vacuum
  2. concentrationconcentrated on rotavap

Sources & evidence

ORD record
ord-64e24624670e4a7da4db24d21400e089
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

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