Ammonium Chloride → 3-(4-Aminophenyl)isothiazolo[5,4-d]pyrimidin-4-amine

HRID 227619Notes

Reaction equation

HRID 227619 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[N:16][C:17]=3[NH2:19])[S:12][N:11]=2)=[CH:6][CH:5]=1)([O-])=O.[NH4+].[Cl-]>[Fe].C(O)C.O>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[N:16][C:17]=3[NH2:19])[S:12][N:11]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 444147423-(4-Nitrophenyl)isothiazolo[5,4-d]pyrimidin-4-amine

Product 1

HCID 444147433-(4-Aminophenyl)isothiazolo[5,4-d]pyrimidin-4-amineYield 97%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

A mixture of Example 96F (0.95 g, 3.5 mmol), iron (0.78 g, 13.9 mmol), and NH4Cl (0.19 g, 3.5 mmol) in 9:1 ethanol/water (80 mL) was heated to 60° C. for 4 hours, cooled to room temperature, and filtered through a pad of diatomaceous earth (Celite®). The pad was washed with THF and the filtrate was concentrated. The concentrate was suspended in water and filtered. The filter cake was washed with water and dried to provide 0.82 g (97% yield) of the desired product.

Workup

  1. filtrationfiltered through a pad of diatomaceous earth (Celite®)
  2. washThe pad was washed with THF
  3. concentrationthe filtrate was concentrated
  4. filtrationfiltered
  5. washThe filter cake was washed with water
  6. customdried

Sources & evidence

ORD record
ord-a460971fa4ed47fbad10cd78486f36e4
Source dataset
uspto-grants-2009_07
Patent number
US07560552B2

Reaction notes

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