Methanol → 2,4-Diamino-6-ethoxypyrimidine

HRID 1947242Notes

Reaction equation

HRID 1947242 reaction equation
[H-].[Na+].[NH2:3][C:4]1[N:9]=[C:8]([OH:10])[CH:7]=[C:6]([NH2:11])[N:5]=1.FC(F)(F)S(O[CH2:18][CH3:19])(=O)=O.CO>CN(C=O)C>[CH2:18]([O:10][C:8]1[N:9]=[C:4]([NH2:3])[N:5]=[C:6]([NH2:11])[CH:7]=1)[CH3:19]

Participants

6

Reactant 4

HCID 887MethanolHCID 24758Sodium hydrideHCID 67924Ethyl trifluoromethanesulphonateHCID 178507952HCID 178507952, compound

Product 1

HCID 2226632,4-Diamino-6-ethoxypyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

174 mg of sodium hydride (60% in mineral oil, 4.36 mmol) are added in portions under an argon atmosphere to a vigorously stirred solution of 500 mg (3.96 mmol) of 2,6-diaminopyrimidin-4-ol in 10 ml of DMF. After 30 min, 700 μl (5.15 mmol) of ethyl trifluoromethanesulfonate are added dropwise, and the solution is stirred for a further 20 min. Methanol (1 ml) is then added to the reaction mixture, which is directly purified by preparative HPLC. Combining the product fractions and removing the solvent result in 370 mg (64% of theory) of the title compound as a white solid.

Workup

  1. customis directly purified by preparative HPLC
  2. customremoving the solvent

Sources & evidence

ORD record
ord-832eba073aa44a17a97c71e3a73ca919
Source dataset
uspto-grants-2013_03
Patent number
US08399471B2

Reaction notes

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