Potassium Carbonate → 4-[3-(4-amino-[1,3,5]triazin-2-yl)-2-methyl-3H-benzoimidazol-5-yl]-1-(tert-butyl-dimethyl-silanyloxy)-2-methyl-but-3-yn-2-ol

HRID 1398707ノート

反応式

HRID 1398707 の反応式
[C:1]([Si:5]([CH3:14])([CH3:13])[O:6][CH2:7][C:8]([CH3:12])([OH:11])[C:9]#[CH:10])([CH3:4])([CH3:3])[CH3:2].Br[C:16]1[CH:17]=[CH:18][C:19]2[N:23]=[C:22]([CH3:24])[N:21]([C:25]3[N:30]=[CH:29][N:28]=[C:27]([NH2:31])[N:26]=3)[C:20]=2[CH:32]=1.C1C=CC(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2].[Cu]I>[NH2:31][C:27]1[N:28]=[CH:29][N:30]=[C:25]([N:21]2[C:20]3[CH:32]=[C:16]([C:10]#[C:9][C:8]([CH3:12])([OH:11])[CH2:7][O:6][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:14])[CH3:13])[CH:17]=[CH:18][C:19]=3[N:23]=[C:22]2[CH3:24])[N:26]=1

参加物

8

反応物 4

HCID 11430Potassium CarbonateHCID 812191,3-Bis(diphenylphosphino)propaneHCID 110959763-Butyn-2-ol, 1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methyl-2 回HCID 681818904-(6-Bromo-2-methyl-benzoimidazol-1-yl)-[1,3,5]triazin-2-ylamine

生成物 1

HCID 681817704-[3-(4-amino-[1,3,5]triazin-2-yl)-2-methyl-3H-benzoimidazol-5-yl]-1-(tert-butyl-dimethyl-silanyloxy)-2-methyl-but-3-yn-2-ol収率 68%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

The title compound was prepared by procedure described in Example 144, by substituting 2-ethynylbicyclo [2.2.1]heptan-2-ol with 1-(tert-butyl-dimethyl-silanyloxy)-2-methyl-but-3-yn-2-ol. A mixture of 4-(6-bromo-2-methyl-benzoimidazol-1-yl)-[1,3,5]triazin-2-ylamine (300 mg, 0.98 mmol), 1-(tert-butyl-dimethyl-silanyloxy)-2-methyl-but-3-yn-2-ol (380 mg, 1.9 mmol) in DMF (2.5 mL) was treated with Pd(OAc)2 (20 mg, 0.1 mmol), dppp (60 mg, 0.2 mmol), CuI (5 mg, 0.05 mmol) and K2CO3 (280 mg, 2.0 mmol), then the mixture was heated at 120° C. for 40 min under microwave. After filtrated and concentrated by vacuum, the residue was purified by silica gel chromatography (DCM: MeOH=20:1) to get the title compound 4-[3-(4-amino-[1,3,5]triazin-2-yl)-2-methyl-3H-benzoimidazol-5-yl]-1-(tert-butyl-dimethyl-silanyloxy)-2-methyl-but-3-yn-2-ol (7-b) (300 mg, yield 68%).

後処理

  1. customThe title compound was prepared by procedure
  2. filtrationAfter filtrated
  3. concentrationconcentrated by vacuum
  4. customthe residue was purified by silica gel chromatography (DCM: MeOH=20:1)

出典と根拠

ORDレコード
ord-e1e7c712b5de4b66b6ed042c7a63e6b9
出典データセット
uspto-grants-2014_12
特許番号
US08901313B2

反応ノート

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