Bromine → 3-{5-Bromo-6-[(2,2-dimethyl-propyl)-methyl-amino]-pyrimidin-4-ylamino}-4,n-dimethyl-benzamide

HRID 1666088ノート

反応式

HRID 1666088 の反応式
[CH3:1][C:2]([CH3:25])([CH3:24])[CH2:3][N:4]([CH3:23])[C:5]1[N:10]=[CH:9][N:8]=[C:7]([NH:11][C:12]2[CH:13]=[C:14]([CH:19]=[CH:20][C:21]=2[CH3:22])[C:15]([NH:17][CH3:18])=[O:16])[CH:6]=1.C(=O)(O)[O-].[Na+].[Br:31]Br>C(Cl)Cl.O>[Br:31][C:6]1[C:7]([NH:11][C:12]2[CH:13]=[C:14]([CH:19]=[CH:20][C:21]=2[CH3:22])[C:15]([NH:17][CH3:18])=[O:16])=[N:8][CH:9]=[N:10][C:5]=1[N:4]([CH2:3][C:2]([CH3:25])([CH3:24])[CH3:1])[CH3:23]

参加物

6

反応物 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 589285053-{6-[(2,2-Dimethyl-propyl)-methyl-amino]-pyrimidin-4-ylamino}-4,N-dimethyl-benzamide

生成物 1

HCID 589285453-{5-Bromo-6-[(2,2-dimethyl-propyl)-methyl-amino]-pyrimidin-4-ylamino}-4,n-dimethyl-benzamide収率 44.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 3-{6-[(2,2-dimethyl-propyl)-methyl-amino]-pyrimidin-4-ylamino}-4,N-dimethyl-benzamide (0.46 g, 1.34 mmol) in methylene chloride (10 mL), was added sat. aq. sodium bicarbonate (2 mL) and bromine (0.07 mL, 1.37 mmol). The resulting mixture was stirred at room temperature for 18 hours, and the reaction was then diluted with water (20 mL). The organic layer was separated and the aqueous layer was extracted with DCM (10 mL). The combined organic layer was dried (sodium sulfate), filtered and concentrated. The residue was purified by silica gel column chromatography using 2% methanol in DCM as eluent to afford the product (250 mg, yield 44%). MS (m/z): 420 (M+H).

後処理

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with DCM (10 mL)
  3. dry with materialThe combined organic layer was dried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-08a4ebad2ab34b59a361cce53c5b126e
出典データセット
uspto-grants-2011_10
特許番号
US08044040B2

反応ノート

読み込み中…