Acetonitrile → 5-(2-(3-(Methylsulfonyl)phenyl)-7-morpholinothiazolo[4,5-d]pyrimidin-5-yl)pyrimidin-2-amine

HRID 1692802ノート

反応式

HRID 1692802 の反応式
Cl[C:2]1[N:3]=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:5]2[S:10][C:9](I)=[N:8][C:6]=2[N:7]=1.[CH3:18][S:19]([C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1)(=[O:21])=[O:20].C(=O)([O-])[O-].[Na+].[Na+].[C:37](#[N:39])[CH3:38]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[CH3:18][S:19]([C:22]1[CH:23]=[C:24]([C:9]2[S:10][C:5]3[C:4]([N:12]4[CH2:17][CH2:16][O:15][CH2:14][CH2:13]4)=[N:3][C:2]([C:38]4[CH:37]=[N:39][C:2]([NH2:7])=[N:3][CH:4]=4)=[N:7][C:6]=3[N:8]=2)[CH:25]=[CH:26][CH:27]=1)(=[O:21])=[O:20]

参加物

7

反応物 4

HCID 6342Acetonitrile2 回HCID 10340Sodium Carbonate2 回HCID 27735423-(Methylsulfonyl)phenylboronic acidHCID 252527634-(5-Chloro-2-iodothiazolo[4,5-d]pyrimidin-7-yl)morpholine

生成物 1

HCID 252549375-(2-(3-(Methylsulfonyl)phenyl)-7-morpholinothiazolo[4,5-d]pyrimidin-5-yl)pyrimidin-2-amine

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒2 回HCID 962Water溶媒2 回

実験手順

5-Chloro-2-iodo-7-morpholinothiazolo[4,5-d]pyrimidine, 3-(methylsulfonyl)phenyl boronic acid and trans-dichlorobis(triphenylphosphine)palladium(II) (0.1 eq) were slurried with equal parts 1M sodium carbonate (3 eq) and acetonitrile. The solution was microwaved at 90° C. for 10 minutes. Water was added and the solution was filtered. The aqueous layer was dried and combined with 5-pyrimidine-2-amine boronic acid (1.2 eq), and trans-dichlorobis(triphenylphosphine)palladium(II) (0.1 eq) were slurried with equal parts 1M sodium carbonate aqueous solution (3 eq) and acetonitrile. The solution was microwaved at 150° C. for 10 minutes. Water was added and the solution was filtered. The resulting precipitate was purified by reverse phase silica gel chromatography to yield 142.

後処理

  1. customThe solution was microwaved at 90° C. for 10 minutes
  2. filtrationthe solution was filtered
  3. customThe aqueous layer was dried
  4. customThe solution was microwaved at 150° C. for 10 minutes
  5. filtrationthe solution was filtered
  6. customThe resulting precipitate was purified by reverse phase silica gel chromatography

出典と根拠

ORDレコード
ord-863dc239127b4ee18ac3cb1cd94b80ea
出典データセット
uspto-grants-2012_04
特許番号
US08158626B2

反応ノート

読み込み中…