Ethylamine → 2-Amino-6-ethylaminopyrimidine

HRID 1666255Notes

Reaction equation

HRID 1666255 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4](C)[N:3]=1.[CH2:10]([NH2:12])[CH3:11]>O>[NH2:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]([NH:12][CH2:10][CH3:11])[N:7]=1

Participants

4

Reactant 2

HCID 6341EthylamineHCID 218102-Amino-4-chloro-6-methylpyrimidine

Product 1

HCID 544617992-Amino-6-ethylaminopyrimidineYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 3-necked 3-L flask, that was equipped with an overhead stirrer, was added in order 2-amino-4-chloro-6-methylpyrimidine (Aldrich, 100 g, 0.696 mol, 1 equiv.), ethylamine (70% ethylamine in water, Lancaster, 625 mL), 625 mL H2O, and 125 mL TEA (0.889 mol, 1.28 equiv.). The mixture was stirred and heated at reflux for 20 h, during which time the reaction turned homogeneous. The reaction was allowed to cool to room temperature. The volatile ethylamine was removed on a rotary evaporator. A precipitate formed. The aqueous mixture containing the precipitate was allowed to stand at room temperature for 2 h and then filtered. After drying under vacuum, 106 g (100% yield) of 2-amino-6-ethylaminopyrimidine was obtained as a colorless solid. This material was used as such in the following reaction.

Workup

  1. customTo a 3-necked 3-L flask, that was equipped with an overhead stirrer
  2. temperatureheated
  3. temperatureat reflux for 20 h, during which time the reaction
  4. customThe volatile ethylamine was removed on a rotary evaporator
  5. customA precipitate formed
  6. additionThe aqueous mixture containing the precipitate
  7. filtrationfiltered
  8. customAfter drying under vacuum

Sources & evidence

ORD record
ord-bcc0450383ee499da686d5b4c0370d8e
Source dataset
uspto-grants-2011_10
Patent number
US08044062B2

Reaction notes

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