Sodium ethoxide → 5-Bromo-2-(2,6-difluorophenyl)pyrimidine-4-carboxylic acid

HRID 69934

反応式

HRID 69934 の反応式
CC[O-].[Na+].Cl.[F:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:8]=1[C:9](=[NH:11])[NH2:10].[C:17]([OH:25])(=[O:24])/[C:18](=[C:20](\[CH:22]=O)/[Br:21])/Br>CCO>[Br:21][C:20]1[C:18]([C:17]([OH:25])=[O:24])=[N:11][C:9]([C:8]2[C:7]([F:6])=[CH:15][CH:14]=[CH:13][C:12]=2[F:16])=[N:10][CH:22]=1

参加物

5

反応物 3

HCID 2723922Sodium ethoxideHCID 3033972Mucobromic AcidHCID 463184242,6-Difluorobenzamidine hydrochloride

生成物 1

HCID 666523345-Bromo-2-(2,6-difluorophenyl)pyrimidine-4-carboxylic acid

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒3 回

実験手順

A 2.68 M NaOEt in EtOH solution (3 eq) was added to an ice-bath cooled mixture of 2,6-difluorobenzimidamide hydrochloride (2 eq) in EtOH (0.1 M). The resulting mixture was allowed to warm to rt and stirred under N2 for 30 min. To the reaction mixture was added drop wise a solution of mucobromic acid (1 eq) in EtOH and the reaction was heated in a 50° C. oil bath for 2.5 hr. After cooling to rt the reaction mixture was concentrated in vacuo. H2O and 1.0 N NaOH were added and the aqueous mixture was washed with EtOAc. The aqueous phase was acidified to pH=4 with 1.0 N HCl then extracted with EtOAc. Combined organic extracts were washed once with brine, then dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to give 5-bromo-2-(2,6-difluorophenyl)pyrimidine-4-carboxylic acid. The crude product was used for the next step without further purification. LC/MS (m/z): 316.9 (MH+). LC: Rt: 2.426 min.

後処理

  1. temperaturecooled
  2. temperaturethe reaction was heated in a 50° C. oil bath for 2.5 hr
  3. temperatureAfter cooling to rt the reaction mixture
  4. concentrationwas concentrated in vacuo
  5. additionH2O and 1.0 N NaOH were added
  6. washthe aqueous mixture was washed with EtOAc
  7. extractionthen extracted with EtOAc
  8. washCombined organic extracts were washed once with brine
  9. dry with materialdried over anhydrous Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-cc678ab9ee294ee5b54fe1b9dddb6206
出典データセット
uspto-grants-2014_09
特許番号
US08822497B2

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