Sodium Dithionite → 5,6-Diamino-1-ethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

HRID 1246239

Reaction equation

HRID 1246239 reaction equation
[NH2:1][C:2]1[N:7]([CH2:8][CH3:9])[C:6](=[O:10])[NH:5][C:4](=[O:11])[C:3]=1[N:12]=O.S(S([O-])=O)([O-])=O.[Na+].[Na+]>N>[NH2:12][C:3]1[C:4](=[O:11])[NH:5][C:6](=[O:10])[N:7]([CH2:8][CH3:9])[C:2]=1[NH2:1]

Participants

4

Reactant 2

HCID 24489Sodium DithioniteHCID 3005096-Amino-1-ethyl-5-nitroso-1,3-dihydropyrimidine-2,4-dione

Product 1

HCID 219163605,6-Diamino-1-ethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of 6-amino-1-ethyl-5-nitroso-1,3-dihydropyrimidine-2,4-dione (3.9 g, 21.2 mmol) in 14.5% aqueous ammonia (50 ml) at 50° C. was added sodium dithionite (Na2S2O4, 7.37 g, 42.4 mmol) in portions over 15 minutes, and the mixture was stirred for 20 minutes. The solution was concentrated under reduced pressure to a volume of 30 ml, cooled to 5° C., the precipitate filtered off, and washed with cold water, to provide 5,6-diamino-1-ethyl-1,3-dihydropyrimidine-2,4-dione, a compound of formula (15).

Workup

  1. concentrationThe solution was concentrated under reduced pressure to a volume of 30 ml
  2. filtrationthe precipitate filtered off
  3. washwashed with cold water

Sources & evidence

ORD record
ord-2443bbfa8f024c93944ecdffc01c0a92
Source dataset
uspto-grants-2006_10
Patent number
US07125993B2

Linked notes

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