Triethylamine → 5-(6-Amino-pyridin-3-ylethynyl)-2-methylsulfanyl-6-(3-trifluoromethyl-phenyl)-pyrimidin-4-ylamine

HRID 1405037Notes

Reaction equation

HRID 1405037 reaction equation
I[C:2]1[C:3]([NH2:20])=[N:4][C:5]([S:18][CH3:19])=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=1.[C:21]([C:23]1[CH:24]=[CH:25][C:26]([NH2:29])=[N:27][CH:28]=1)#[CH:22].C(N(CC)CC)C>CN(C=O)C.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:29][C:26]1[N:27]=[CH:28][C:23]([C:21]#[C:22][C:2]2[C:3]([NH2:20])=[N:4][C:5]([S:18][CH3:19])=[N:6][C:7]=2[C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)=[CH:24][CH:25]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 219548275-Ethynylpyridin-2-amineHCID 585134235-Iodo-2-methylsulfanyl-6-(3-trifluoromethyl-phenyl)-pyrimidin-4-ylamine

Product 1

HCID 585131525-(6-Amino-pyridin-3-ylethynyl)-2-methylsulfanyl-6-(3-trifluoromethyl-phenyl)-pyrimidin-4-ylamine

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

The title compound is synthesized according to general procedure GP2 starting from 850 mg (2.1 mmol) 5-iodo-2-methylsulfanyl-6-(3-trifluoromethyl-phenyl)-pyrimidin-4-ylamine, 1.5 g (12.4 mmol) 5-ethynyl-2-amino-pyridine, 39 mg (0.21 mmol) CuI, 145 mg (0.21 mmol) PdCl2(PPh3)2 and 2.9 mL triethylamine in 15 mL dry DMF. Yield after purification by RP-HPLC: 427 mg (52%).

Workup

  1. customYield
  2. customafter purification by RP-HPLC

Sources & evidence

ORD record
ord-2e56bca242f8424ebe5ea47606ea5e0c
Source dataset
uspto-grants-2014_12
Patent number
US08916548B2

Reaction notes

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