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Formic Acid → N-(2-Pyrimidinyl)-formamide

HRID 622664
Notes
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Reaction equation

HRID 622664 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 284Formic AcidHCID 297MethaneHCID 24489Sodium DithioniteHCID 13015879Nitropyrimidine

Product 1

HCID 255580N-(2-Pyrimidinyl)-formamide

Reagents, catalysts & solvents 2

HCID 713FormamideSolvent
On this pageParticipantsProcedureWorkupSources & evidenceReaction notes
HCID 962
Water
Solvent

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 additonal 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 additonal 20-25 minutes
  2. filtrationfiltered through celite
  3. temperaturecooled
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-76eb27d0c56d47229585af694d469fe7
Source dataset
uspto-grants-1988_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04772606

Reaction notes

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