Ammonium Chloride → HCID 71256125, compound

HRID 388440Notes

Reaction equation

HRID 388440 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[N:4]([C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][N:20]=2)[N:3]=1.[NH4+].[Cl-]>CO.C1COCC1.O.[Fe]>[NH2:25][C:22]1[CH:23]=[CH:24][C:19]([N:4]2[C:5]3=[N:6][CH:7]=[N:8][C:9]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[C:10]3[C:2]([I:1])=[N:3]2)=[N:20][CH:21]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 71256051HCID 71256051, compound

Product 1

HCID 71256125HCID 71256125, compoundYield 58.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 21892291Methanol tetrahydrofuran waterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of tert-butyl 3-iodo-1-(5-nitropyridin-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylcarbamate (62) (4 g, 8.28 mmol) in a mixture of MeOH/THF/H2O (50 mL/50 mL/10 mL) was added Fe (2.61 g, 46.6 mmol) and NH4Cl (4.98 g, 93.1 mmol). The mixture was stirred at 60° C. under N2 for 3 h and then filtered through a Celite pad. The filtrate was concentrated in vacuo. The residue was purified by column chromatography (silica gel, 0 to 10% MeOH in DCM) to give tert-butyl 1-(5-aminopyridin-2-yl)-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-ylcarbamate (63) (2.2 g, 52%) as a light yellow solid. LC-MS (ESI): m/z (M+1) 454.

Workup

  1. filtrationfiltered through a Celite pad
  2. concentrationThe filtrate was concentrated in vacuo
  3. customThe residue was purified by column chromatography (silica gel, 0 to 10% MeOH in DCM)

Sources & evidence

ORD record
ord-c8bf329bfe5c44c29de79c8cb5abf7a9
Source dataset
uspto-grants-2013_02
Patent number
US08377946B1

Reaction notes

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