Sodium Dithionite → 5,6-Diamino-3-propylpyrimidine-2,4(1H,3H)-dione

HRID 1929731Notes

Reaction equation

HRID 1929731 reaction equation
[NH2:1][C:2]1[NH:7][C:6](=[O:8])[N:5]([CH2:9][CH2:10][CH3:11])[C:4](=[O:12])[C:3]=1[N:13]=O.S(S([O-])=O)([O-])=O.[Na+].[Na+]>N>[NH2:13][C:3]1[C:4](=[O:12])[N:5]([CH2:9][CH2:10][CH3:11])[C:6](=[O:8])[NH:7][C:2]=1[NH2:1]

Participants

4

Reactant 2

HCID 24489Sodium DithioniteHCID 144253236-Amino-5-nitroso-3-propylpyrimidine-2,4(1H,3H)-dione

Product 1

HCID 109542025,6-Diamino-3-propylpyrimidine-2,4(1H,3H)-dione

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of 6-amino-5-nitroso-3-propyl-1,3-dihydropyrimidine-2,4-dione (5.4 g, 27 mmol) in 12.5% aqueous ammonia (135 ml) at 70° C. was added sodium dithionite (Na2S2O4, 9.45 g, 54 mmol) in portions over 15 minutes, and the mixture was stirred for 20 minutes. The solution was concentrated under reduced pressure, cooled to 5° C., the precipitate filtered off, and washed with cold water, to provide 5,6-diamino-3-propyl-1,3-dihydropyrimidine-2,4-dione, a compound of formula (12).

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. filtrationthe precipitate filtered off
  3. washwashed with cold water

Sources & evidence

ORD record
ord-8d44119292d84afdbb51cb9fac7406b4
Source dataset
uspto-grants-2012_05
Patent number
US08188099B2

Reaction notes

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