6-Amino-3-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione → 6-Amino-3-methyl-5-nitroso-1,2,3,4-tetrahydropyrimidine-2,4-dione

HRID 2200539Notes

Reaction equation

HRID 2200539 reaction equation
[NH2:1][C:2]1[NH:7][C:6](=[O:8])[N:5]([CH3:9])[C:4](=[O:10])[CH:3]=1.[N:11]([O-])=[O:12].[Na+]>C(O)(=O)C.O>[NH2:1][C:2]1[NH:7][C:6](=[O:8])[N:5]([CH3:9])[C:4](=[O:10])[C:3]=1[N:11]=[O:12]

Participants

5

Reactant 2

HCID 8169076-Amino-3-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dioneHCID 23668193Sodium Nitrite

Product 1

HCID 32477206-Amino-3-methyl-5-nitroso-1,2,3,4-tetrahydropyrimidine-2,4-dione

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of 6-amino-3-methylpyrimidine-2,4(1H,3H)-dione (6 g, 42.6 mmol) in acetic acid (50 mL) was added a solution of sodium nitrite (6.8 g, 98.6 mmol) in water (20 mL) dropwise, then the mixture was stirred at room temperature for 1 h. The mixture was filtered, the filter cake was washed with water and ethanol and dried under vacuum to give 6-amino-3-methyl-5-nitrosopyrimidine-2,4(1H,3H)-dione as violet solid, which was used directly in the next step.

Workup

  1. filtrationThe mixture was filtered
  2. washthe filter cake was washed with water and ethanol
  3. customdried under vacuum

Sources & evidence

ORD record
ord-a5c52915cff341119d919b04d6caef8e
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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