Sodium Dithionite → SS-3364

HRID 2200540Notes

Reaction equation

HRID 2200540 reaction equation
[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.S(S([O-])=O)([O-])=O.[Na+].[Na+]>[OH-].[NH4+]>[NH2:11][C:3]1[C:4](=[O:10])[N:5]([CH3:9])[C:6](=[O:8])[NH:7][C:2]=1[NH2:1]

Participants

4

Reactant 2

HCID 24489Sodium DithioniteHCID 32477206-Amino-3-methyl-5-nitroso-1,2,3,4-tetrahydropyrimidine-2,4-dione

Product 1

HCID 1201412SS-3364Yield 30.1%

Reagents, catalysts & solvents 1

HCID 14923Ammonium HydroxideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 6-amino-3-methyl-5-nitrosopyrimidine-2,4(1H,3H)-dione in ammonium hydroxide (100 mL) was added sodium hydrosulfite (6.8 g, 39.1 mmol) in small portions at 70° C., the mixture was stirred at 70° C. for 1 h. The mixture was concentrated and ice-water was added. The slurry was filtered and the filter cake was washed with water and ethanol and dried under vacuum to give 5,6-diamino-3-methylpyrimidine-2,4(1H,3H)-dione (2.0 g, 30.1% yield over two steps) as yellow solid. LCMS MH+ 157.

Workup

  1. concentrationThe mixture was concentrated
  2. additionice-water was added
  3. filtrationThe slurry was filtered
  4. washthe filter cake was washed with water and ethanol
  5. customdried under vacuum

Sources & evidence

ORD record
ord-1ab726b5306d4b009486b00b20057be0
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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