Hydroxyamine hydrochloride → 3-Amino-5,7-dimethyl[1,2]oxazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

HRID 2164449Notes

Reaction equation

HRID 2164449 reaction equation
Cl[C:2]1[N:7]([CH3:8])[C:6](=[O:9])[N:5]([CH3:10])[C:4](=[O:11])[C:3]=1[C:12]#[N:13].[OH2:14].O.O.C([O-])(=O)C.[Na+].Cl.[NH2:23]O>CO>[NH2:13][C:12]1[O:14][N:23]=[C:2]2[C:3]=1[C:4](=[O:11])[N:5]([CH3:10])[C:6](=[O:9])[N:7]2[CH3:8]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 122056876-chloro-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrileHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 126779883-Amino-5,7-dimethyl[1,2]oxazolo[3,4-d]pyrimidine-4,6(5H,7H)-dioneYield 87.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.4 g of 6-chloro-5-cyano-1,3-dimethyluracil was stirred together with a mixture of 150 ml of methanol, 6.0 g of sodium acetate trihydrate and 3.0 g of hydroxylamine hydrochloride at room temperature for 3 hours. Resulting precipitates were recovered by filtration and washed with 10 ml of water twice and then with 5 ml of methanol. The precipitates were recrystallized from dimethylformamide-water to give 1.2 g of light yellow prisms, melting point: 280°-284° C. (decomp.). Ultraviolet absorption spectrum: λmax H2O 266 nm (ε=8780)

Workup

  1. customResulting
  2. customprecipitates
  3. filtrationwere recovered by filtration
  4. washwashed with 10 ml of water twice
  5. customThe precipitates were recrystallized from dimethylformamide-water

Sources & evidence

ORD record
ord-53875e96dfa74603bd23951d1cb22111
Source dataset
uspto-grants-1985_03
Patent number
US04504662

Reaction notes

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