Methanol → 6-Methoxypyrimidine-2,4-diamine

HRID 2201380Notes

Reaction equation

HRID 2201380 reaction equation
[Na].[NH2:2][C:3]1[N:8]=[C:7]([NH2:9])[CH:6]=[C:5](Cl)[N:4]=1.[Na+].[Cl-].[CH3:13][OH:14]>>[CH3:13][O:14][C:5]1[N:4]=[C:3]([NH2:2])[N:8]=[C:7]([NH2:9])[CH:6]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 5234Sodium ChlorideHCID 674322,4-Diamino-6-chloropyrimidineHCID 5360545Sodium

Product 1

HCID 8169256-Methoxypyrimidine-2,4-diamine

Procedure

To a solution of 9.2 g (0.40 mol) sodium in 320 ml methanol were added 28.9 g (0.20 mol) 2,4-diamino-6-chloropyrimidine. The mixture was heated under reflux with stirring for 44 h. After the reaction was ended the precipitated NaCl was separated off and the solution was concentrated to dryness. The residue in 300 ml ethanol was heated to boiling and filtered hot. The product precipitated out of the filtrate on standing overnight. Recrystallization of the mother liquor likewise afforded product. After drying, 6-methoxy-2,4-diaminopyrimidine was obtained as a white solid (58.8 g, 84%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux
  3. customwas separated off
  4. concentrationthe solution was concentrated to dryness
  5. temperatureThe residue in 300 ml ethanol was heated
  6. filtrationfiltered hot
  7. customThe product precipitated out of the filtrate
  8. waiton standing overnight
  9. customRecrystallization of the mother liquor likewise afforded product
  10. customAfter drying

Sources & evidence

ORD record
ord-9abd4842632d420aace3cdf457dee8c8
Source dataset
uspto-grants-2016_06
Patent number
US09364407B2

Reaction notes

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