1-(4-methoxybenzyl)-3-methyl-4-(5-nitropyrimidin-2-yloxy)-1H-pyrazolo[3,4-b]pyridine → 2-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)pyrimidin-5-amine

HRID 2241313Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:29]=[CH:28][C:6]([CH2:7][N:8]2[C:12]3=[N:13][CH:14]=[CH:15][C:16]([O:17][C:18]4[N:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][N:19]=4)=[C:11]3[C:10]([CH3:27])=[N:9]2)=[CH:5][CH:4]=1>CCO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:12]3=[N:13][CH:14]=[CH:15][C:16]([O:17][C:18]4[N:19]=[CH:20][C:21]([NH2:24])=[CH:22][N:23]=4)=[C:11]3[C:10]([CH3:27])=[N:9]2)=[CH:28][CH:29]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A 250 mL round-bottomed flask was charged with 1-(4-methoxybenzyl)-3-methyl-4-(5-nitropyrimidin-2-yloxy)-1H-pyrazolo[3,4-b]pyridine (0.420 g, 1.07 mmol), SnCl2 dihydrate (1.45 g, 6.42 mmol), and EtOH (100 mL). The reaction mixture was heated to 70° C. under nitrogen for 2 hours, then concentrated in vacuo. The residue was diluted with EtOAc, water, and brine. Aqueous saturated Na2CO3 was added until the pH was in the 9-10 range. The combined organic phases were dried (Na2SO4). The product was isolated by filtration and flash chromatography (EtOAc/MeOH 95:5) to afford 0.10 g (25%). LRMS M+1 (363.0) observed.

Workup

concentrationconcentrated in vacuo
additionThe residue was diluted with EtOAc, water, and brine
additionAqueous saturated Na2CO3 was added until the pH
dry with materialThe combined organic phases were dried (Na2SO4)
customThe product was isolated by filtration and flash chromatography (EtOAc/MeOH 95:5)
customto afford 0.10 g (25%)

Sources & evidence

ORD record: ord-4f02a8dc0b85425aa253b00941c9167e
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723330B2

Reaction notes

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