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

HRID 495028Notes

Reaction equation

HRID 495028 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-15f42c2af4364369bcd5d39fdece8d1c
Source dataset
uspto-grants-2009_05
Patent number
US07538214B2

Reaction notes

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