Sodium Dithionite → 5,6-diamino-1-benzylpyrimidine-2,4(1H,3H)-dione

HRID 2213847Notes

Reaction equation

HRID 2213847 reaction equation
[NH2:1][C:2]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6](=[O:15])[NH:5][C:4](=[O:16])[C:3]=1[N:17]=O.S(S([O-])=O)([O-])=O.[Na+].[Na+]>N>[NH2:17][C:3]1[C:4](=[O:16])[NH:5][C:6](=[O:15])[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:2]=1[NH2:1]

Participants

4

Reactant 2

HCID 24489Sodium DithioniteHCID 33071146-amino-1-benzyl-5-nitrosopyrimidine-2,4(1H,3H)-dione

Product 1

HCID 107520325,6-diamino-1-benzylpyrimidine-2,4(1H,3H)-dione

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

To a solution of 6-amino-5-nitroso-1-benzyl-1,3-dihydropyrimidine-2,4-dione (1.15 g, 4.7 mmol) in 12.5% aqueous ammonia (40 ml) at 70° C. was added sodium hydrosulfite (2.44 g, 14 mmol) in portions over 15 minutes. On cooling the reaction mixture in an ice bath the product precipitated out. It was filtered, washed with water, and dried under reduced pressure, to provide 5,6-diamino-1-benzyl-1,3-dihydropyrimidine-2,4-dione, a compound of formula (21).

Workup

  1. temperatureOn cooling the reaction mixture in an ice bath the product
  2. customprecipitated out
  3. filtrationIt was filtered
  4. washwashed with water
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-f1851c22b7d34bc6ba4b8d608ffcbf3f
Source dataset
uspto-grants-2006_09
Patent number
US07105665B2

Reaction notes

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