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

HRID 1868487노트

반응식

HRID 1868487 반응식
[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]

참가 물질

5

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 46901747HCID 46901747, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
50 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2ad21cf2df844537bc6bce73311aa874
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07635699B2

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