Sodium Dithionite → 7,8-Dihydropteridine

HRID 616252Notes

Reaction equation

HRID 616252 reaction equation
N[C:2]1[N:7]=[C:6](O)[C:5]([N+]([O-])=O)=[C:4]([NH:12][C:13](CC)(CC)[C:14](=[N:17]O)CO)[N:3]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+].N1C2C(=NC=CN=2)C=NC1>[OH-].[Na+]>[N:3]1[C:4]2[NH:12][CH2:13][CH:14]=[N:17][C:5]=2[CH:6]=[N:7][CH:2]=1

Participants

5

Reactant 3

HCID 24489Sodium DithioniteHCID 21880558HCID 21880558, compoundHCID 178446283HCID 178446283, compound

Product 1

HCID 189641747,8-DihydropteridineYield 70.3%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

2-Amino-4-hydroxy-6-(3-hydroxy-2-hydroxyimino-1-spirocyclohexylpropylamino)-5-nitropyrimidine (II) (500 mg) was dissolved in the minimum of 0.1M sodium hydroxide by warming on the steam bath. Sodium dithionite was added portionwise until an almost colourless solution was obtained. On cooling the dihydropteridine separated and was filtered off and purified by dissolving in 2M HCl and reprecipitated by the addition of 0.88 ammonia to pH8. On standing the dihydropteridine (I) (150 mg; yield 38%) was obtained as a pale yellow crystalline solid, m.p. >300 (decomp.).

Workup

  1. temperatureby warming on the steam bath
  2. customwas obtained
  3. customseparated
  4. filtrationwas filtered off
  5. custompurified
  6. dissolutionby dissolving in 2M HCl
  7. customreprecipitated by the addition of 0.88 ammonia to pH8

Sources & evidence

ORD record
ord-bd3aa916ab024ab4b6a80a9e33b69739
Source dataset
uspto-grants-1978_02
Patent number
US04073786

Reaction notes

Loading…