Sodium Hydroxide → (2R)-4-[2-(2-Aminopyrimidin-5-yl)-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-8-yl]-2-methylpiperazine-1-carboaldehyde

HRID 1876602ノート

反応式

HRID 1876602 の反応式
[CH3:1][C@H:2]1[NH:7][CH2:6][CH2:5][N:4]([C:8]2[N:9]([CH2:30][C:31]([F:34])([F:33])[F:32])[C:10]3[C:15]([N:16]=2)=[C:14]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[N:13]=[C:12]([C:23]2[CH:24]=[N:25][C:26]([NH2:29])=[N:27][CH:28]=2)[N:11]=3)[CH2:3]1.[CH3:35]N(CCS(O)(=O)=O)C.[OH-:44].[Na+]>O1CCCC1>[NH2:29][C:26]1[N:27]=[CH:28][C:23]([C:12]2[N:11]=[C:10]3[C:15]([N:16]=[C:8]([N:4]4[CH2:5][CH2:6][N:7]([CH:35]=[O:44])[C@H:2]([CH3:1])[CH2:3]4)[N:9]3[CH2:30][C:31]([F:34])([F:32])[F:33])=[C:14]([N:17]3[CH2:18][CH2:19][O:20][CH2:21][CH2:22]3)[N:13]=2)=[CH:24][N:25]=1

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 2370422-(Dimethylamino)ethanesulfonic acidHCID 593335845-{8-[(3R)-3-Methylpiperazin-1-yl]-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-2-yl}pyrimidin-2-amine

生成物 1

HCID 59333567(2R)-4-[2-(2-Aminopyrimidin-5-yl)-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-8-yl]-2-methylpiperazine-1-carboaldehyde収率 90%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

5-{8-[(3R)-3-Methylpiperazin-1-yl]-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-2-yl}pyrimidin-2-amine (101.9 mg, 0.21 mmol) was added to a tetrahydrofuran solution (5.0 ml) of 1H-benzotriazole-1-carboxyaldehyde (34.8 mg, 0.21 mmol) at room temperature and the resulting mixture was stirred for 105 minutes. The reaction mixture was poured into a 2 N aqueous sodium hydroxide solution and the resulting mixture was extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate, the mixture was filtrated, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer silica gel chromatography (methylene chloride:methanol=10:1) to give the title compound (96.8 mg, 90%) as a pale yellow solid.

後処理

  1. extractionthe resulting mixture was extracted with methylene chloride
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationthe mixture was filtrated
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customthe resulting residue was purified by preparative thin layer silica gel chromatography (methylene chloride:methanol=10:1)

出典と根拠

ORDレコード
ord-a474daafa87c4a1cb6c9eb042250d473
出典データセット
uspto-grants-2012_11
特許番号
US08309546B2

反応ノート

読み込み中…