Dihydroxyacetone → 2,4-Diamino-6-hydroxymethylpteridine

HRID 1729704Notes

Reaction equation

HRID 1729704 reaction equation
C([O-])(=O)C.[Na+].S(=O)(O)[O-].[OH:10][CH2:11][C:12]([CH2:14]O)=O.Cl.N[C@H](C(O)=O)CS.Cl.Cl.[NH2:26][C:27]1[N:32]=[C:31]([NH2:33])[C:30]([NH2:34])=[C:29]([NH2:35])[N:28]=1>O>[NH2:26][C:27]1[N:32]=[C:31]([NH2:33])[C:30]2[C:29](=[N:35][CH:14]=[C:12]([CH2:11][OH:10])[N:34]=2)[N:28]=1

Participants

7

Reactant 5

HCID 670DihydroxyacetoneHCID 60960Cysteine HydrochlorideHCID 104748BisulfiteHCID 517045Sodium AcetateHCID 12365029Pyrimidine-2,4,5,6-tetramine--hydrogen chloride (1/2)

Product 1

HCID 703472,4-Diamino-6-hydroxymethylpteridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 128 grams of sodium acetate, 136 grams of bisulphite addition product of 1,3-dihydroxyacetone (free of methyl glyoxal) and 46 grams of cysteine hydrochloride in 390 ml water was prepared at room temperature in a 2 liter three-necked flask fitted with a stirrer, an air-bubbling system and a dropping funnel. To this solution, the 400 ml of the previously prepared solution of 2,4,5,6-tetraaminopyrimidine dihydrochloride were added with energic stirring and air-bubbling. A solution of 8 g of selenium dioxide dissolved in the minimum amount of water was made. Half of this solution was added to the reaction mixture immediately after the addition of the tetraaminopyrimidine solution and the other half 4-7 hours later.

Workup

  1. customwas prepared at room temperature in a 2 liter three-necked flask
  2. customfitted with a stirrer
  3. customair-bubbling
  4. dissolutionA solution of 8 g of selenium dioxide dissolved in the minimum amount of water
  5. additionHalf of this solution was added to the reaction mixture
  6. additionimmediately after the addition of the tetraaminopyrimidine solution
  7. customthe other half 4-7 hours

Sources & evidence

ORD record
ord-23c6fb1ca509424c817b8fe28e89140b
Source dataset
uspto-grants-1976_11
Patent number
US03989703

Reaction notes

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