Ammonium Chloride → 4-[3-(3-aminophenyl)-1-(4-methoxybenzyl)-1H-pyrazol-4-yl]pyrimidin-2-amine

HRID 45876Notes

Reaction equation

HRID 45876 reaction equation
[CH3:1][O:2][C:3]1[CH:30]=[CH:29][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([NH2:19])[N:14]=3)[C:10]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-])=O)[CH:21]=3)=[N:9]2)=[CH:5][CH:4]=1.[Cl-].[NH4+]>O1CCOCC1.O.[Zn]>[NH2:26][C:22]1[CH:21]=[C:20]([C:10]2[C:11]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([NH2:19])[N:14]=3)=[CH:12][N:8]([CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:30][CH:29]=3)[N:9]=2)[CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 67184232HCID 67184232, compound

Product 1

HCID 671841854-[3-(3-aminophenyl)-1-(4-methoxybenzyl)-1H-pyrazol-4-yl]pyrimidin-2-amineYield 67.5%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

1.6 g (3.98 mmol) of 4-[1-(4-methoxybenzyl)-3-(3-nitrophenyl)-1H-pyrazol-4-yl]-pyrimidin-2-amine were dissolved in a mixture of 100 ml of dioxane and 30 ml of water and 2.12 g (40 mmol) of ammonium chloride and 1.05 g (16 mmol) of metallic zinc were added successively. The reaction mixture was stirred at 100° C. for 6 hours. The suspension was then filtered through a celite pad and the filtrate evaporated. The residue was partitioned between dichloromethane and aqueous sodium hydrogenocarbonate, dried over sodium sulphate and evaporated again, giving 1 g (67%) of the title compound.

Workup

  1. additionwere added successively
  2. filtrationThe suspension was then filtered through a celite pad
  3. customthe filtrate evaporated
  4. customThe residue was partitioned between dichloromethane and aqueous sodium hydrogenocarbonate
  5. dry with materialdried over sodium sulphate
  6. customevaporated again

Sources & evidence

ORD record
ord-f357b4c759c74524888692fa8d860ef6
Source dataset
uspto-grants-2013_09
Patent number
US08541575B2

Reaction notes

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