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 1398707노트

반응식

HRID 1398707 반응식
[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

참가 물질

8

반응물 4

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

생성물 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-ol수율 68%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

반응 조건

온도
120 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-e1e7c712b5de4b66b6ed042c7a63e6b9
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901313B2

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