Ammonium Chloride → 2-(3-aminophenoxy)-9-isopropyl-N-(1-methyl-1H-pyrazol-4-yl)-9H-purin-6-amine

HRID 928168Notes

Reaction equation

HRID 928168 reaction equation
[CH:1]([N:4]1[CH:12]=[N:11][C:10]2[C:5]1=[N:6][C:7]([O:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-])=O)[CH:22]=1)=[N:8][C:9]=2[NH:13][C:14]1[CH:15]=[N:16][N:17]([CH3:19])[CH:18]=1)([CH3:3])[CH3:2].[NH4+].[Cl-]>CCOC(C)=O.O.[Fe]>[NH2:27][C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][CH:24]=1)[O:20][C:7]1[N:6]=[C:5]2[C:10]([N:11]=[CH:12][N:4]2[CH:1]([CH3:3])[CH3:2])=[C:9]([NH:13][C:14]2[CH:15]=[N:16][N:17]([CH3:19])[CH:18]=2)[N:8]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 1180735689-isopropyl-N-(1-methyl-1H-pyrazol-4-yl)-2-(3-nitrophenoxy)-9H-purin-6-amine

Product 1

HCID 1180736312-(3-aminophenoxy)-9-isopropyl-N-(1-methyl-1H-pyrazol-4-yl)-9H-purin-6-amineYield 100%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 9-isopropyl-N-(1-methyl-1H-pyrazol-4-yl)-2-(3-nitrophenoxy)-9H-purin-6-amine (50 mg, 0.14 mmol), Fe (39 mg, 0.7 mmol), NH4Cl (75 mg, 1.4 mmol) in EtOAc (10 mL) and water (10 mL) was stirred at rt overnight. The mixture was filtered and the filtrate was extracted with EtOAc (2×10 mL). The combined organic layers were dried over Na2SO4 and concentrated to give crude product (46 mg, 100% yield), which was used the next step directly without further purification.

Workup

  1. filtrationThe mixture was filtered
  2. extractionthe filtrate was extracted with EtOAc (2×10 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6830f154a47444248291f70bb4749d55
Source dataset
uspto-grants-2016_03
Patent number
US09290496B2

Reaction notes

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