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

HRID 2063218Notes

Reaction equation

HRID 2063218 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-6eeb59e3729e445eb24188114aeab459
Source dataset
uspto-grants-2012_10
Patent number
US08288318B2

Reaction notes

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