Formic Acid → formamidopyrimidine

HRID 728800Notes

Reaction equation

HRID 728800 reaction equation
[N+:1]([C:4]1[N:9]=[CH:8][CH:7]=[CH:6][N:5]=1)([O-])=O.[CH:10](O)=[O:11].S(S([O-])=O)([O-])=O.[Na+].[Na+].C>C(N)=O.O>[CH:10]([NH:1][C:4]1[N:9]=[CH:8][CH:7]=[CH:6][N:5]=1)=[O:11]

Participants

7

Reactant 4

HCID 284Formic AcidHCID 297MethaneHCID 24489Sodium DithioniteHCID 130158792-Nitropyrimidine

Product 1

HCID 255580formamidopyrimidine

Reagents, catalysts & solvents 2

HCID 713FormamideSolventHCID 962WaterSolvent

Procedure

The crude nitropyrimidine (25.32 g) from above was suspended in formamide (150 ml) and 90% formic acid (50 ml) and the suspension was warmed to 70° C. in a water bath. Sodium dithionite was carefully added to the warm suspension and then boiled for 15-20 minutes. The reaction mixture was diluted with hot water (300 ml), treated with charcoal and then boiled for an additional 20-25 minutes, filtered through celite, cooled and concentrated under reduced pressure to give formamido-pyrimidine which was collected by filtration, washed with acetone, and dried under vacuum at 56° C.

Workup

  1. waitboiled for an additional 20-25 minutes
  2. filtrationfiltered through celite
  3. temperaturecooled
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c46ab75fdd594a259230d073dd0aae3c
Source dataset
uspto-grants-1991_09
Patent number
US05051429

Reaction notes

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