Triethylamine → HCID 58513107, compound

HRID 1405027Notes

Reaction equation

HRID 1405027 reaction equation
[C:1]([O:5][C:6](=[O:27])[NH:7][C:8]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[C:10]([C:18]2[C:23](I)=[C:22]([CH3:25])[N:21]=[C:20]([NH2:26])[N:19]=2)[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]#[CH:36])=[CH:31][N:30]=1.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>[C:1]([O:5][C:6](=[O:27])[NH:7][C:8]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[C:10]([C:18]2[C:23]([C:36]#[C:35][C:32]3[CH:31]=[N:30][C:29]([NH2:28])=[CH:34][CH:33]=3)=[C:22]([CH3:25])[N:21]=[C:20]([NH2:26])[N:19]=2)[CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 219548275-Ethynylpyridin-2-amineHCID 58513333HCID 58513333, compound

Product 1

HCID 58513107HCID 58513107, compound

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 733 mg (1.5 mmol) [3-(2-amino-5-iodo-6-methyl-pyrimidin-4-yl)-5-trifluoromethyl-phenyl]-carbamic acid tert-butyl ester (A-41) and 262 mg (2.2 mmol) 2-amino-5-ethynyl-pyridine (A-15) using 28 mg (0.15 mmol) CuI, 104 mg (0.15 mmol) PdCl2(PPh3)2 and 2 mL (15 mmol) triethylamine in 14 mL dry DMF. For the work-up the solvent is removed in vacuo and the product is purified by chromatography on silica gel (DCM/MeOH gradient). Yield: 632 mg (88%).

Workup

  1. customFor the work-up the solvent is removed in vacuo
  2. customthe product is purified by chromatography on silica gel (DCM/MeOH gradient)

Sources & evidence

ORD record
ord-e735b31e751645ee99428765424781e7
Source dataset
uspto-grants-2014_12
Patent number
US08916548B2

Reaction notes

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