Trifluoroacetic acid → 4-N-(N,N-dimethyl-aminomethylene)-1-methylcytosine

HRID 1509951Notes

Reaction equation

HRID 1509951 reaction equation
[NH:1]1[CH:8]=[CH:7][C:5]([NH2:6])=[N:4][C:2]1=[O:3].F[C:10](F)(F)C(O)=O.CO[CH:18](OC)[N:19]([CH3:21])[CH3:20]>>[CH3:18][N:19]([CH:21]=[N:6][C:5]1[CH:7]=[CH:8][N:1]([CH3:10])[C:2](=[O:3])[N:4]=1)[CH3:20]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 78373Dimethylformamide dimethyl acetalHCID 178418229Cytosine

Product 1

HCID 126802844-N-(N,N-dimethyl-aminomethylene)-1-methylcytosine

Conditions

Temperature
120 °C

Procedure

Cytosine (3.0 g, 27 mmol) and dimethyl-formamide-dimethylacetal (40 mL) was added to 100 mL mad apple-type flask with a magnetic stirrer, heated at 120° C. with constant stirring. Then, trifluoroacetic acid (0.2 mL) was added and the mixture was allowed to stir for 18 hr. The reacting solution was cooled to room temperature, followed by cooling in ice bath. The white precipitation was filtrated, dissolved in dichloromethane and ethanol, and changed to powders by hexane. The solids were collected and dried under vacuum. Thus, 4-N—(N,N-dimethylaminomethylene)-1-methylcytosine was obtained as white solids (3.6 g, yield, 74%). 1H-NMR (400 MHz, DMSO-d6)

Workup

  1. temperatureThe reacting solution was cooled to room temperature
  2. temperatureby cooling in ice bath
  3. customThe white precipitation
  4. filtrationwas filtrated
  5. dissolutiondissolved in dichloromethane
  6. customThe solids were collected
  7. customdried under vacuum

Sources & evidence

ORD record
ord-368cd4e56ec44743a69b16d6a64a8551
Source dataset
uspto-grants-2012_07
Patent number
US08211899B2

Reaction notes

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