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

HRID 1246235Notes

Reaction equation

HRID 1246235 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-9df93f57d9e3402fb16290214eb87b4f
Source dataset
uspto-grants-2006_10
Patent number
US07125993B2

Reaction notes

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