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 1398707Notes

Reaction equation

HRID 1398707 reaction equation
[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

Participants

8

Reactant 4

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

Product 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-olYield 68%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-e1e7c712b5de4b66b6ed042c7a63e6b9
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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