2-Amino-4,6-dichloropyrimidine → 2-Pyrimidinamine, 4-chloro-6-methoxy-

HRID 1920819Notes

Reaction equation

HRID 1920819 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[C:4]([NH2:9])[N:3]=1.[CH3:10][O-:11].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[C:6]([O:11][CH3:10])[N:5]=[C:4]([NH2:9])[N:3]=1

Participants

4

Reactant 2

HCID 655222-Amino-4,6-dichloropyrimidineHCID 10942334Sodium Methoxide

Product 1

HCID 798112-Pyrimidinamine, 4-chloro-6-methoxy-Yield 90.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 4,6-dichloro-2-amino pyrimidine (5.0 g, 30.5 mmol) in MeOH (100 mL) was added 25% sodium methoxide (6.59 g, 30.5 mmol). The solution was refluxed for 20 hours, at which time the methanol was removed in vacuo. The residue was dissolved in EtOAc (350 mL), washed with H2O (100 mL) and with NaCl(sat.) (100 mL), dried over Na2SO4, filtered and concentrated yielding 4.4 g (90%) of 4-chloro-6-methoxypyrimidine-2-ylamine.

Workup

  1. customwas removed in vacuo
  2. dissolutionThe residue was dissolved in EtOAc (350 mL)
  3. washwashed with H2O (100 mL) and with NaCl(sat.) (100 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-63fe651a60c84f3eba66a37ea164a5f1
Source dataset
uspto-grants-2012_05
Patent number
US08173647B2

Reaction notes

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