Hydrochloric Acid → 5,6-Diamino-1,3-dipropyl-2,4(1H,3H)-pyrimidinedione

HRID 1262529Notes

Reaction equation

HRID 1262529 reaction equation
[NH2:1][C:2]1[C:3](=[O:15])[N:4]([CH2:12][CH2:13][CH3:14])[C:5](=[O:11])[N:6]([CH2:8][CH2:9][CH3:10])[CH:7]=1.[N:16]([O-])=O.[Na+].Cl.S(S([O-])=O)([O-])=O.[Na+].[Na+].[OH-].[Na+]>O>[NH2:1][C:2]1[C:3](=[O:15])[N:4]([CH2:12][CH2:13][CH3:14])[C:5](=[O:11])[N:6]([CH2:8][CH2:9][CH3:10])[C:7]=1[NH2:16]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24489Sodium DithioniteHCID 194315655-Amino-1,3-dipropylpyrimidine-2,4(1H,3H)-dioneHCID 23668193Sodium Nitrite

Product 1

HCID 50986055,6-Diamino-1,3-dipropyl-2,4(1H,3H)-pyrimidinedioneYield 60.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 5-amino-1,3-dipropyl-2,4-(1H,3H)-pyrimidinedione (52.8 g, 0.25 moles), sodium nitrite (20.7 g, 0.30 moles) and water (1000 ml) is prepared and treated with hydrochloric acid (12 N, 30 ml, 0.35 moles) after the method of Blicke (J. Am. Chem. Soc., 76, 2798 (1954)]. 6-Amino-1,3-dipropyl-5-nitroso-2,4-(1H,3H)pyrmidinedione is collected as described and is used as obtained in the next step. The nitroso compound is suspended in water (500 ml) and treated with sodium dithionite, added portionwise in a quantity sufficient to effect decolorization of the purple nitroso compound. The resulting slurry is treated with sodium hydroxide (100 ml 50%), chilled, and filtered. The solids thus obtained are dried at 78° in a vacuum oven to yield 34.4 g of 5,6-diamino-1,3-dipropyl-2,4-(1H,3H)pyrimidinedione.

Workup

  1. customis prepared
  2. custom6-Amino-1,3-dipropyl-5-nitroso-2,4-(1H,3H)pyrmidinedione is collected
  3. customas obtained in the next step
  4. additionadded portionwise in a quantity sufficient
  5. temperaturechilled
  6. filtrationfiltered
  7. customThe solids thus obtained
  8. customare dried at 78° in a vacuum oven

Sources & evidence

ORD record
ord-6297c7883cda4f6280283646b3e9d580
Source dataset
uspto-grants-1984_06
Patent number
US04452788

Reaction notes

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