Ammonia → Methyl 6-amino-2-chloropyrimidine-4-carboxylate

HRID 2063219Notes

Reaction equation

HRID 2063219 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9](S(C)(=O)=O)[N:8]=[C:7]([Cl:15])[N:6]=1)=[O:4].[NH3:16]>O1CCOCC1.CO>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9]([NH2:16])[N:8]=[C:7]([Cl:15])[N:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 84031284Methyl 2-chloro-6-(methylsulfonyl)pyrimidine-4-carboxylate

Product 1

HCID 53396493Methyl 6-amino-2-chloropyrimidine-4-carboxylateYield 85%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

2-Chloro-6-methanesulfonylpyrimidine-4-carboxylic acid methyl ester (3.7 g, 14.75 mmol) was dissolved in dioxane and 7N ammonia in methanol was added. The reaction mixture was stirred at room temperature for 3 hours, concentrated under vacuum, and the residue partitioned between ethyl acetate and water. The organic phase was dried and concentrated. The product was purified by column chromatography to provide 6-amino-2-chloropyrimidine-4-carboxylic acid methyl ester (2.35 g, 85% yield): 1H NMR (DMSO-d6): δ 7.6 (br s, 1H), 7.00 (s, 1H), 3.84 (s, 3H), 3.33 (s, 3H).

Workup

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

Sources & evidence

ORD record
ord-84e977c233344377a800a6c2aa8fd841
Source dataset
uspto-grants-2012_10
Patent number
US08288318B2

Reaction notes

Loading…