2-Amino-4-chloropyrimidine → 4-Methoxy-2-pyrimidinamine

HRID 872296

Reaction equation

HRID 872296 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[N:3]=1.[CH3:9][O-:10].[Na+]>CO>[CH3:9][O:10][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[N:3]=1

Participants

4

Reactant 2

HCID 2233322-Amino-4-chloropyrimidineHCID 10942334Sodium Methoxide

Product 1

HCID 674284-Methoxy-2-pyrimidinamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 4-chloro-pyrimidin-2-ylamine (10 g, 77 mmol) in methanol (400 mL) under argon, was treated with a solution of sodium methoxide in methanol (25.7%, 51.59 mL, 0.232 mol) whereupon a cream yellow solution was obtained. The reaction was heated at reflux for 3 hours to give a clear yellow green solution. On cooling the volatiles were removed in vacuo and the residue taken up in 100 mL EtOAc and washed with 100 mL water. The organic phase was dried, filtered and concentrated in vacuo to give the title compound as a white solid (9.12 g).

Workup

  1. customwas obtained
  2. temperatureThe reaction was heated
  3. temperatureat reflux for 3 hours
  4. customto give a clear yellow green solution
  5. temperatureOn cooling the volatiles
  6. customwere removed in vacuo
  7. washwashed with 100 mL water
  8. customThe organic phase was dried
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c192c0921800477bb0d096d57c361c97
Source dataset
uspto-grants-2015_03
Patent number
US08975265B2

Linked notes

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