Hydroxyamine hydrochloride → 5-Chloro-8-methoxy[1,2,4]triazolo[1,5-c]pyrimidin-2-amine

HRID 2197418Notes

Reaction equation

HRID 2197418 reaction equation
Cl.[NH2:2]O.C(=O)(O)[O-].[Na+].[Cl:9][C:10]1[N:15]=[C:14]([NH:16][C:17]([NH:19]C(=O)OCC)=S)[C:13]([O:25][CH3:26])=[CH:12][N:11]=1>O.C(O)(C)(C)C.C(=O)([O-])[O-].[Na+].[Na+]>[Cl:9][C:10]1[N:15]2[N:19]=[C:17]([NH2:2])[N:16]=[C:14]2[C:13]([O:25][CH3:26])=[CH:12][N:11]=1

Participants

7

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 56949522Ethyl [(2-chloro-5-methoxypyrimidin-4-yl)amino]carbonothioylcarbamate

Product 1

HCID 569495765-Chloro-8-methoxy[1,2,4]triazolo[1,5-c]pyrimidin-2-amine

Reagents, catalysts & solvents 3

HCID 10340Sodium CarbonateCatalystHCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

Hydroxylamine hydrochloride (280 mg, 4 eq), and sodium bicarbonate (210 mg, 2.5 eq) were combined in water (5 mL) and stirred for 5 minutes. Ethyl [(2-chloro-5-methoxypyrimidin-4-yl)amino]carbonothioylcarbamate (2) (290 mg, 1.0 mmol), suspended in t-butanol (15 mL) was added at room temperature. The reaction was stirred at room temperature for 5 hours, and then treated with 10 drops of saturated aqueous sodium carbonate solution. The reaction slurry was then filtered, and the product solids washed with water and dried to obtain the title compound as a off white solid (330 mg, 83%) that was identical in HPLC retention to previously described 5-chloro-8-methoxy[1,2,4]triazolo-[1,5-c]pyrimidin-2-amine (4).

Workup

  1. additionwas added at room temperature
  2. stirringThe reaction was stirred at room temperature for 5 hours
  3. filtrationThe reaction slurry was then filtered
  4. washthe product solids washed with water
  5. customdried

Sources & evidence

ORD record
ord-ef436f6bd67f4994b814df23fa7ae02d
Source dataset
uspto-grants-2012_12
Patent number
US08338596B2

Reaction notes

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