6-Amino-1-methyl-5-nitrosouracil → HCID 178481641, compound

HRID 1744764Notes

Reaction equation

HRID 1744764 reaction equation
[NH2:1][C:2]1[N:7]([CH3:8])[C:6](=[O:9])[NH:5][C:4](=[O:10])[C:3]=1[N:11]=O.OS([O-])=O.[Na+].[NH2:18]C1C(=O)NC(=O)N(C)C=1N.N([O-])=O.[Na+]>O.C(O)(=O)C>[CH3:8][N:7]1[C:2]2[NH:1][N:18]=[N:11][C:3]=2[C:4](=[O:10])[NH:5][C:6]1=[O:9]

Participants

7

Reactant 4

HCID 814486-Amino-1-methyl-5-nitrosouracilHCID 1571843-Methyl-4,5-diaminouracilHCID 23665763Sodium BisulfiteHCID 23668193Sodium Nitrite

Product 1

HCID 178481641HCID 178481641, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent3×

Conditions

Temperature
0 °C

Procedure

To a suspersion of 2.42 g (14.3 mmol) of the 6-amino-1-methyl-5-nitrosouracil in water heated to 90° C., was added 30 mL of a 38% solution of NaHSO3 over 10 minutes and the reaction allowed to continue until the reaction mixture was completely decolourized. After cooling the reaction mixture to 0° C., 5,6-diamino-1-methyluracil crystallized from the medium. After filtering off, washing with water, ethanol and diethylether and drying 2.14 g (80%) of the intermediate 5,6-diamino-1-methyluracil was isolated. 8.71 g (55.8 mmol) of 5,6-diamino-1-methyluracil was dissolved in 100 mL water and 50 mL acetic acid upon heating. After cooling to room temperature, a solution of 3.86 g (55.9 mmol) NaNO2 in 17 mL water was added over 5 minutes. The mixture was stirred for 5 minutes and then refluxed for a short time. After standing for two days at room temperature, 3-methyl-8-aza-9H-xanthine crystallized from the mixture. After filtering off, drying, recrystallization from water/ethanol 1:1 and drying 3.57 g (38%) of 3-methyl-8-aza-9H-xanthine was obtained (m.p. 313–320° C.).

Workup

  1. custom5,6-diamino-1-methyluracil crystallized from the medium
  2. filtrationAfter filtering off
  3. washwashing with water, ethanol and diethylether
  4. dry with materialdrying 2.14 g (80%) of the intermediate 5,6-diamino-1-methyluracil
  5. customwas isolated
  6. temperatureAfter cooling to room temperature
  7. temperaturerefluxed for a short time
  8. waitAfter standing for two days at room temperature
  9. custom3-methyl-8-aza-9H-xanthine crystallized from the mixture
  10. filtrationAfter filtering off
  11. customdrying
  12. customrecrystallization from water/ethanol 1:1
  13. dry with materialdrying 3.57 g (38%) of 3-methyl-8-aza-9H-xanthine
  14. customwas obtained (m.p. 313–320° C.)

Sources & evidence

ORD record
ord-7f8c8fe87e944fc7a04e453767dcd3b2
Source dataset
uspto-grants-2006_03
Patent number
US07018786B2

Reaction notes

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