Ammonium Hydroxide → 5,6-Diamino-1,3-dipropyl-2,4(1H,3H)-pyrimidinedione

HRID 3655

Reaction equation

HRID 3655 reaction equation
[CH2:1]([N:4]1[C:11]([NH2:12])=[C:10]([N:13]=O)[C:8](=[O:9])[N:7]([CH2:15][CH2:16][CH3:17])[C:5]1=[O:6])[CH2:2][CH3:3].[OH-].[NH4+].S(S([O-])=O)([O-])=O.[Na+].[Na+]>O>[CH2:1]([N:4]1[C:11]([NH2:12])=[C:10]([NH2:13])[C:8](=[O:9])[N:7]([CH2:15][CH2:16][CH3:17])[C:5]1=[O:6])[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 24489Sodium DithioniteHCID 51820186-Amino-5-nitroso-1,3-dipropylpyrimidine-2,4(1H,3H)-dione

Product 1

HCID 50986055,6-Diamino-1,3-dipropyl-2,4(1H,3H)-pyrimidinedioneYield 64.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The 1,3-di-n-propyl-5-nitroso-6-aminouracil (61.6 g) was suspended in 1 L of water, and the suspension was made alkaline to pH 11 with 50% ammonium hydroxide and treated with 100 g of sodium dithionite, in portions, until the purple color faded. The aqueous mixture was extracted with chloroform (8×200 ml), dried over magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography (5/10% methanol/chloroform) and recrystallized from 10% isopropanol in hexane and recrystallized from 10% isopropanol to yield 37.29 g of 1,3-di-n-propyl-5,6-diaminouracil, m.p., 127°-128° C.

Workup

  1. extractionThe aqueous mixture was extracted with chloroform (8×200 ml)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (5/10% methanol/chloroform)
  6. customrecrystallized from 10% isopropanol in hexane
  7. customrecrystallized from 10% isopropanol

Sources & evidence

ORD record
ord-7844fca8b36648daa76fa1325c5434bd
Source dataset
uspto-grants-1998_03
Patent number
US05734052

Linked notes

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