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

HRID 2189000
Notes
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Reaction equation

HRID 2189000 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-acb7e75928c7461da7938677b10d615b
Source dataset
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08324224B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes