Ammonia → Methyl 6-amino-2,5-dichloropyrimidine-4-carboxylate

HRID 1593971Notes

Reaction equation

HRID 1593971 reaction equation
[NH3:1].[CH3:2][O:3][C:4]([C:6]1[C:11]([Cl:12])=[C:10](Cl)[N:9]=[C:8]([Cl:14])[N:7]=1)=[O:5]>O1CCOCC1>[CH3:2][O:3][C:4]([C:6]1[C:11]([Cl:12])=[C:10]([NH2:1])[N:9]=[C:8]([Cl:14])[N:7]=1)=[O:5]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 248061Methyl 2,5,6-trichloropyrimidine-4-carboxylate

Product 1

HCID 312630Methyl 6-amino-2,5-dichloropyrimidine-4-carboxylateYield 87%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Ammonia was bubbled through a solution of 2,5,6-trichloro-pyrimidine-4-carboxylic acid methyl ester (15.94 g, 66 mmol, see H. Gershon, J. Org. Chem. 1962, 27, 3507-3510 for preparation) in p-dioxane (150 mL) for 30 minutes. The solvent was then removed and the residue partitioned between ethyl acetate and water. The organic phase was dried and concentrated under vacuum. The product was purified by column chromatography to provide 6-amino-2,5-dichloropyrimidine-4-carboxylic acid methyl ester (12.74 g, 87% yield): mp 164-166° C.

Workup

  1. customThe solvent was then removed
  2. customthe residue partitioned between ethyl acetate and water
  3. customThe organic phase was dried
  4. concentrationconcentrated under vacuum
  5. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-687f4d4435574c22bb9ad5e0c82ad2d3
Source dataset
uspto-grants-2007_11
Patent number
US07300907B2

Reaction notes

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