Ethylene Glycol → HCID 22639954, compound

HRID 2201389Notes

Reaction equation

HRID 2201389 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[C:4](Cl)[N:3]=1.[Na].[CH2:11]([OH:14])[CH2:12][OH:13]>O>[NH2:1][C:2]1[N:3]=[C:4]([O:13][CH2:12][CH2:11][OH:14])[CH:5]=[C:6]([NH2:8])[N:7]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 674322,4-Diamino-6-chloropyrimidineHCID 5360545Sodium

Product 1

HCID 22639954HCID 22639954, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

28.9 g (0.20 mol) of 2,4-diamino-6-chloropyrimidine was added to a solution of 4.6 g (0.20 mol) of sodium in 124 ml of ethylene glycol and heated to 80° C. for 44 h while stirring was performed. After termination of the reaction, the solution was diluted with 300 ml of water and extracted with tert-butyl methyl ether (5×200 ml). The combined organic phases were discarded; a precipitate precipitated out of the aqueous phases. The precipitate was washed with water; after drying, 2-[(2,6-diaminopyrimidin-4-yl)oxy]ethan-1-ol (16.1 g, 47%) was obtained as a light-beige solid.

Workup

  1. customAfter termination of the reaction
  2. extractionextracted with tert-butyl methyl ether (5×200 ml)
  3. customa precipitate precipitated out of the aqueous phases
  4. washThe precipitate was washed with water
  5. customafter drying

Sources & evidence

ORD record
ord-2f33c2ddc49c4cd99ddbad2d9f2b7c19
Source dataset
uspto-grants-2016_06
Patent number
US09364408B2

Reaction notes

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