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

HRID 2233104ノート

反応式

HRID 2233104 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-4872f388b23949c1b64f44e98b9f77e5
出典データセット
uspto-grants-2010_05
特許番号
US07709468B2

反応ノート

読み込み中…