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

HRID 1496888Notes

Reaction equation

HRID 1496888 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-b4ec5a1d11434b419ee5a58a6b05fef2
Source dataset
uspto-grants-2015_12
Patent number
US09199943B2

Reaction notes

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