Pyridine → Tert. butyl 6-chloro-5-methyl-pyrimidine-4-carboxylate

HRID 74618Notes

Reaction equation

HRID 74618 reaction equation
N1C=CC=CC=1.[C:7]([OH:11])([CH3:10])([CH3:9])[CH3:8].[Cl:12][C:13]1[N:18]=[CH:17][N:16]=[C:15]([C:19](Cl)=[O:20])[C:14]=1[CH3:22]>ClCCl>[Cl:12][C:13]1[N:18]=[CH:17][N:16]=[C:15]([C:19]([O:11][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:20])[C:14]=1[CH3:22]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6386tert-ButanolHCID 580351066-Chloro-5-methyl-pyrimidine-4-carboxylic acid chloride

Product 1

HCID 58386606Tert. butyl 6-chloro-5-methyl-pyrimidine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

At 0° C. a solution of 5.8 mL pyridine and 15 mL tert.-butanol in 10 mL dichloromethane was added dropwise to 6.0 g 6-chloro-5-methyl-pyrimidine-4-carboxylic acid chloride in 10 mL dichloromethane. The reaction mixture was heated to RT and stirred for 30 min. The reaction mixture was diluted with dichloromethane and washed successively with a 2M sodium hydroxide solution, twice with a 10% aqueous citric acid solution and a sodium chloride solution. The organic phase was dried and evaporated down. The residue was taken up in dichloromethane and purified by flash chromatography. The product-containing fractions were evaporated down and dried.

Workup

  1. washwashed successively with a 2M sodium hydroxide solution, twice with a 10% aqueous citric acid solution
  2. customThe organic phase was dried
  3. customevaporated down
  4. custompurified by flash chromatography
  5. customThe product-containing fractions were evaporated down
  6. customdried

Sources & evidence

ORD record
ord-20e77411c4a14424be18a038fb809bd7
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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