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

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	1,3-Bis(diphenylphosphino)propane	HCID 81219	—
Reactant	3-Butyn-2-ol, 1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methyl-	HCID 11095976	—
Reactant	4-(6-Bromo-2-methyl-benzoimidazol-1-yl)-[1,3,5]triazin-2-ylamine	HCID 68181890	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	palladium(II) acetate	HCID 167845	—
Solvent	Dimethylformamide	HCID 6228	—
Product	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	HCID 68181770	68%

Reaction Conditions

Temperature	120 °C

Reaction Steps

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%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08901313B2
Source dataset	uspto-grants-2014_12
ORD ID	ord-e1e7c712b5de4b66b6ed042c7a63e6b9
Source note	uspto-grants-2014_12