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

HRID 1496889Notes

Reaction equation

HRID 1496889 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-7fa35a2c219e45019678e4d93c68dcf3
Source dataset
uspto-grants-2015_12
Patent number
US09199943B2

Reaction notes

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