Ammonium Chloride → HCID 86689035, compound

HRID 920204Notes

Reaction equation

HRID 920204 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][CH:20]=2)[N:3]=1.[NH4+].[Cl-]>C1COCC1.CCO.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)=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 71256098HCID 71256098, compound

Product 1

HCID 86689035HCID 86689035, compoundYield 86.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 18504229Ethanol tetrahydrofuran waterSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of tert-butyl 3-iodo-1-(4-nitrophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylcarbamate (28) (4.29 g, 8.7 mmol) in THF/EtOH/H2O (40 mL/20 mL/10 mL) was added Fe powder (2.43 g, 43.45 mmol) and NH4Cl (4.65 g, 86.9 mmol). The resulting mixture was purged with N2 before heated to 50° C. for 2 h. The mixture was cooled and filtered through a Celite pad. The solvents were evaporated and the residue was separated in DCM and water. The aqueous layer was extracted with DCM (×4). The combined organic layers were dried over Na2SO4. Solvent was removed under vacuum and purified by flash chromatography (0-60% EA in PE with 0.5% TEA) to provide tert-butyl 1-(4-aminophenyl)-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-ylcarbamate (29) (3.4 g, 86%) as a yellow solid. LC-MS (ESI): m/z (M+1) 453.0.

Workup

  1. customThe resulting mixture was purged with N2
  2. temperatureThe mixture was cooled
  3. filtrationfiltered through a Celite pad
  4. customThe solvents were evaporated
  5. customthe residue was separated in DCM
  6. extractionThe aqueous layer was extracted with DCM (×4)
  7. dry with materialThe combined organic layers were dried over Na2SO4
  8. customSolvent was removed under vacuum
  9. custompurified by flash chromatography (0-60% EA in PE with 0.5% TEA)

Sources & evidence

ORD record
ord-79093ce62cac4158a7344ab8a565fde7
Source dataset
uspto-grants-2016_03
Patent number
US09273051B2

Reaction notes

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