Sodium Carbonate → 8-Cyclopropylmethyl-2-(4-fluorophenyl)-3-(2-methanesulfonylpyrimidin-4-yl)imidazo[1,2-a]pyrazine

HRID 2233104노트

반응식

HRID 2233104 반응식
[CH:1]1([CH2:4][C:5]2[C:6]3[N:7]([C:11]([C:21]4[CH:26]=[CH:25][N:24]=[C:23](SC)[N:22]=4)=[C:12]([C:14]4[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=4)[N:13]=3)[CH:8]=[CH:9][N:10]=2)[CH2:3][CH2:2]1.O[O:30][S:31]([O-:33])=O.[K+].[C:35]([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl.CO.O>[CH:1]1([CH2:4][C:5]2[C:6]3[N:7]([C:11]([C:21]4[CH:26]=[CH:25][N:24]=[C:23]([S:31]([CH3:35])(=[O:33])=[O:30])[N:22]=4)=[C:12]([C:14]4[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=4)[N:13]=3)[CH:8]=[CH:9][N:10]=2)[CH2:2][CH2:3]1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 23707502Potassium hydroxy sulfiteHCID 588695358-Cyclopropylmethyl-2-(4-fluorophenyl)-3-(2-methylsulfanylpyrimidin-4-yl)imidazo[1,2-a]pyrazine

생성물 1

HCID 588695518-Cyclopropylmethyl-2-(4-fluorophenyl)-3-(2-methanesulfonylpyrimidin-4-yl)imidazo[1,2-a]pyrazine수율 85%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

To a solution of 8-cyclopropylmethyl-2-(4-fluorophenyl)-3-(2-methylsulfanylpyrimidin-4-yl)imidazo[1,2-a]pyrazine (5.16 g, 13.2 mmol) in DCM (50 mL) and MeOH (50 mL) was added a solution of Oxone® (16.2 g, 26.4 mmol) in water (50 mL). After about 4 h of rapid stirring, the mixture was neutralized with saturated Na2CO3 solution and extracted with DCM. The combined organic phase was dried over Na2SO4 and concentrated. The crude material was purified by silica gel chromatography with heptane/EtOAc (gradient 50-100% EtOAc). After concentration, the residue was three times re-dissolved in DCM and re-concentrated to give 4.77 g (85%) of the title compound as a yellowish solid: LC/MS (Table 1, Method g) Rt=2.68 min; MS m/z: 424.1 (M+H)+.

후처리

  1. extractionextracted with DCM
  2. dry with materialThe combined organic phase was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe crude material was purified by silica gel chromatography with heptane/EtOAc (gradient 50-100% EtOAc)
  5. concentrationAfter concentration
  6. dissolutionre-dissolved in DCM
  7. concentrationre-concentrated

출처 및 근거

ORD 기록
ord-4872f388b23949c1b64f44e98b9f77e5
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07709468B2

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