Potassium Carbonate → 4-{6-[4-(Tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-but-1-ynyl]2-methyl-benzoimidazol-1-yl}-[1,3,5]triazin-2-ylamine

HRID 1398704Notes

Reaction equation

HRID 1398704 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([CH3:10])[N:7]([C:11]3[N:16]=[CH:15][N:14]=[C:13]([NH2:17])[N:12]=3)[C:6]=2[CH:18]=1.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].[C:54]([Si:58]([O:61][CH2:62][C:63]([CH3:67])([CH3:66])[C:64]#[CH:65])([CH3:60])[CH3:59])([CH3:57])([CH3:56])[CH3:55]>CN(C)C=O.CC([O-])=O.CC([O-])=O.[Pd+2].[Cu]I>[C:54]([Si:58]([CH3:59])([CH3:60])[O:61][CH2:62][C:63]([CH3:67])([CH3:66])[C:64]#[C:65][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([CH3:10])[N:7]([C:11]3[N:16]=[CH:15][N:14]=[C:13]([NH2:17])[N:12]=3)[C:6]=2[CH:18]=1)([CH3:56])([CH3:57])[CH3:55]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 812191,3-Bis(diphenylphosphino)propaneHCID 681818904-(6-Bromo-2-methyl-benzoimidazol-1-yl)-[1,3,5]triazin-2-ylamineHCID 86669580Tert-butyl-(2,2-dimethyl-but-3-ynyloxy)-dimethyl-silane

Product 1

HCID 681816574-{6-[4-(Tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-but-1-ynyl]2-methyl-benzoimidazol-1-yl}-[1,3,5]triazin-2-ylamineYield 66%

Reagents, catalysts & solvents 3

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

Procedure

In a solution of 4-(6-bromo-2-methyl-benzoimidazol-1-yl)-[1,3,5]triazin-2-ylamine (0.15 g, 0.5 mmol) in N,N-dimethyl-formamide (3 ml) were added 1,3-bis(diphenylphosphino)propane (40 mg, 0.1 mmol), Pd(OAc)2 (10 mg, 0.05 mmol), K2CO3 (207 mg, 1.5 mmol), tert-butyl-(2,2-dimethyl-but-3-ynyloxy)-dimethyl-silane (150 mg, 1 mmol) and CuI (5 mg, 0.025 mmol). Then the solution bubbled N2 for 5 min and was microwaved for 1 h at 120° C. under nitrogen. The reaction mixture was filtrated and the filtrate was purified by column to afford 4-{6-[4-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-but-1-ynyl]2-methyl-benzoimidazol-1-yl}-[1,3,5]triazin-2-ylamine (140 mg, 66%): LCMS m/z=+437.0 (M+H)+.

Workup

  1. customThen the solution bubbled N2 for 5 min
  2. customwas microwaved for 1 h at 120° C. under nitrogen
  3. filtrationThe reaction mixture was filtrated
  4. customthe filtrate was purified by column

Sources & evidence

ORD record
ord-320538e1388348e881d87b8d80226407
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

Loading…