Ammonia → Adenine

HRID 435453Notes

Reaction equation

HRID 435453 reaction equation
[Cl-].Cl[CH:3](Cl)[NH:4][CH:5]=[NH2+:6].[C:8]([O-])(=O)[CH3:9].[NH4+:12].[CH:13]([NH2:15])=O.[NH3:16]>>[N:4]1[C:5]([NH2:6])=[C:9]2[C:8]([N:16]=[CH:13][NH:15]2)=[N:12][CH:3]=1

Participants

5

Reactant 4

HCID 222AmmoniaHCID 713Formamide2×HCID 517165Ammonium AcetateHCID 178479570HCID 178479570, compound

Product 1

HCID 190AdenineYield 41.5%

Conditions

Temperature
40 °C

Procedure

DAMN (0.727 g; 0.1 mole), N-dichloromethylformamidinium chloride (0.12 g; 0.01 mole) and ammonium acetate (0.51 g; 0.01 mole) were charged to a 3 oz. Aerosol Compatibility Tube (Fischer and Porter Co.) at room temperature. An ammoniacal formamide solution consisting of 15 ml of formamide and 0.343 g ammonia was then added to the tube. The reaction was run for 2 hours at 100° C. with magnetic stirring. The mixture was cooled to 40° C. and a black solid by-product which formed during the reaction was filtered. HPLC indicated an adenine yield of 41.5%.

Workup

  1. customat room temperature
  2. additionwas then added to the tube
  3. customa black solid by-product which formed during the reaction
  4. filtrationwas filtered

Sources & evidence

ORD record
ord-2e786863ea5d4beb9d9773306e93e871
Source dataset
uspto-grants-1983_08
Patent number
US04401814

Reaction notes

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