Triethylamine → HCID 58513234, compound

HRID 1405032Notes

Reaction equation

HRID 1405032 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[N:5]=[C:4]([NH2:9])[C:3]=1I.[C:11]([C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)#[CH:12].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>[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[N:5]=[C:4]([NH2:9])[C:3]=1[C:12]#[C:11][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 1860033-EthynylpyridineHCID 58513369HCID 58513369, compound

Product 1

HCID 58513234HCID 58513234, 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 1.0 g (3.7 mmol) 6-chloro-5-iodo-pyrimidine-2,4-diamine, 494 g (4.79 mmol) 3-ethynylpyridine, 70 mg (0.37 mmol) CuI, 259 mg (0.37 mmol) PdCl2(PPh3)2 and 85 mL triethylamine in 60 mL dry DMF. Yield after purification by chromatography on silica gel: 800 mg (88%).

Workup

  1. customYield
  2. customafter purification by chromatography on silica gel

Sources & evidence

ORD record
ord-02b40fdf90b94bf4ae3fdb016078d297
Source dataset
uspto-grants-2014_12
Patent number
US08916548B2

Reaction notes

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