Lithium hydroxide, monohydrate → (+)-6-(Azidomethyl)-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-2-carboxylic acid

HRID 1868487ノート

反応式

HRID 1868487 の反応式
[N:1]([CH2:4][C:5]1[C:6]([CH3:27])=[N:7][C:8]2[N:9]([CH:19]=[C:20]([C:22]([O:24]CC)=[O:23])[N:21]=2)[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1[Cl:18])=[N+:2]=[N-:3].O[Li].O>C1COCC1.O>[N:1]([CH2:4][C:5]1[C:6]([CH3:27])=[N:7][C:8]2[N:9]([CH:19]=[C:20]([C:22]([OH:24])=[O:23])[N:21]=2)[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1[Cl:18])=[N+:2]=[N-:3]

参加物

5

反応物 2

HCID 168937Lithium hydroxide, monohydrateHCID 46901747HCID 46901747、化合物

生成物 1

HCID 46901748(+)-6-(Azidomethyl)-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-2-carboxylic acid収率 94%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

To a stirred solution of (+)-ethyl 6-(azidomethyl)-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-2-carboxylate (1 g, 2.47 mmol) in THF (20 mL) and H2O (2 mL) was added LiOH.H2O (155 mg, 3.70 mmol). After heating to 50° C. for 16 h, the reaction was concentrated under reduced pressure and diluted with EtOAc. The aqueous layer was acidified by 1N HCl to pH=1. The organic layer was washed with satd aq NH4Cl and brine before drying over MgSO4. Filtration, concentration under reduced pressure provided (+)-6-(azidomethyl)-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-2-carboxylic acid (874 mg, 94%) as a white solid.

後処理

  1. concentrationthe reaction was concentrated under reduced pressure
  2. additiondiluted with EtOAc
  3. washThe organic layer was washed with satd aq NH4Cl and brine
  4. dry with materialbefore drying over MgSO4
  5. filtrationFiltration, concentration under reduced pressure

出典と根拠

ORDレコード
ord-2ad21cf2df844537bc6bce73311aa874
出典データセット
uspto-grants-2009_12
特許番号
US07635699B2

反応ノート

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