Methylamine → 1-Methylcytosine

HRID 1509952Notes

Reaction equation

HRID 1509952 reaction equation
CN(C=[N:5][C:6]1[CH:11]=[CH:10][N:9]([CH3:12])[C:8](=[O:13])[N:7]=1)C.CN>C(O)C>[CH3:12][N:9]1[CH:10]=[CH:11][C:6]([NH2:5])=[N:7][C:8]1=[O:13]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 126802844-N-(N,N-dimethyl-aminomethylene)-1-methylcytosine

Product 1

HCID 791431-Methylcytosine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-N—(N,N-dimethyl-aminomethylene)-1-methylcytosine (1.0 g, 5.5 mmol) and ethanol solution (50 mL) containing 30% methylamine were added in 100 mL mad apple-type flask with a magnetic stirrer and the mixture was allowed to stir for 12 hr. The precipitated white solids were collected, and recrystallized in ethanol-water mixture. The object was obtained as white solids (0.61 g, yield, 88%). 1H NMR (400 MHz, DMSO-d6):3.31 (s, 3H), 5.59 (d, 1H), 6.91 (br, 2H), 7.54 (d, 1H) 13C NMR (100 MHz, DMSO-d6):δ6.6, 92.9, 146.6, 156.3, 166.1; MS (ES1+) calcd for C5H7N3O+(M+H+) 126.0662, found 126.0804.

Workup

  1. additionwere added in 100 mL mad apple-type flask with a magnetic stirrer
  2. customThe precipitated white solids were collected
  3. customrecrystallized in ethanol-water mixture
  4. customThe object was obtained as white solids (0.61 g, yield, 88%)

Sources & evidence

ORD record
ord-25443e1bcea34326b3895e5687a2e657
Source dataset
uspto-grants-2012_07
Patent number
US08211899B2

Reaction notes

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