Acetic Acid → 4,6-Diaminopyrimidine-2-sulfinic acid

HRID 260152Notes

Reaction equation

HRID 260152 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([NH2:8])[N:5]=[C:4]([SH:9])[N:3]=1.OO.C(O)(=[O:14])C.[OH-:16].[Na+]>>[NH2:1][C:2]1[CH:7]=[C:6]([NH2:8])[N:5]=[C:4]([S:9]([OH:14])=[O:16])[N:3]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 1785079174,6-diaminopyrimidine-2-thiol

Product 1

HCID 2438514,6-Diaminopyrimidine-2-sulfinic acid

Procedure

To a solution of 50 g of 4,6-diamino-2-mercaptopyrimidine (Aldrich, Milwaukee, Wis., USA) in 2N NaOH (220 mL) was added 750 mL of a 3% hydrogen peroxide solution. The solution was maintained at a temperature less than 20° C. Stirring was continued for a further 30 minutes and the clear pale yellow solution was acidified with acetic acid (ca. 50 mL). The precipitate was washed with H2O and air dried, to give 33 as 58 g (95% yield) of an off-white amorphous acid (m.p. 168°-170° C. decomp.). For analysis, a sample was dissolved in dilute aqueous ammonia and reprecipitated with acetic acid.

Workup

  1. temperatureThe solution was maintained at a temperature less than 20° C
  2. washThe precipitate was washed with H2O and air
  3. customdried

Sources & evidence

ORD record
ord-77b7fb16307b4b0eac92827464e40530
Source dataset
uspto-grants-1996_06
Patent number
US05525711

Reaction notes

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