Triethylamine → HCID 69229367, compound

HRID 1517928Notes

Reaction equation

HRID 1517928 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[C:12]#[CH:13].Cl[C:15]1[CH:20]=[CH:19][N:18]=[C:17](NC)[N:16]=1.[CH2:23]([N:25](CC)CC)C>CN(C)C=O.[Cu]I>[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[C:12]#[C:13][C:19]1[CH:20]=[CH:15][N:16]([NH:25][CH3:23])[CH2:17][N:18]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 640700412947-53-6HCID 123976804-Chloro-N-methylpyrimidin-2-amine

Product 1

HCID 69229367HCID 69229367, compoundYield 84.8%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
71 °C

Procedure

3.0 g (17 mmol) of methyl 4-amino-3-ethynylbenzoate and 2.6 g (19 mmol) of 4-chloro-2-methylaminopyrimidine were initially charged in 20 ml of dimethylformamide (DMF) and 8.7 g (85 mmol) of triethylamine, and degassed with argon while stirring for 5 min. Subsequently, 65 mg of copper(I) iodide and 20 mg of tetrakis(triphenylamine)palladium(0) were added and the mixture was heated to 71° C. for 3 h. After aqueous workup, 4.1 g of methyl 4-amino-3-(1-methylaminopyrimidin-4-yl)ethynylbenzoate were obtained. (HPLC: 99.7 area %) HPLC method as in example 1.

Sources & evidence

ORD record
ord-c1c5e82dcff84b1eb637209e8b6980da
Source dataset
uspto-grants-2012_07
Patent number
US08232395B2

Reaction notes

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