Triethylamine → HCID 58513353, compound

HRID 1405033Notes

Reaction equation

HRID 1405033 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]=[CH:15][C:16]([NH2:19])=[N: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>[NH2:19][C:16]1[N:17]=[CH:18][C:13]([C:11]#[C:12][C:3]2[C:4]([NH2:9])=[N:5][C:6]([NH2:8])=[N:7][C:2]=2[Cl:1])=[CH:14][CH:15]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 219548275-Ethynylpyridin-2-amineHCID 58513369HCID 58513369, compound

Product 1

HCID 58513353HCID 58513353, 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 850 mg (3.1 mmol) 6-chloro-5-iodo-pyrimidine-2,4-diamine, 2.2 g (19 mmol) 5-ethynyl-2-amino-pyridine, 59 mg (0.31 mmol) CuI, 218 mg (0.31 mmol) PdCl2(PPh3)2 and 21 mL triethylamine in 25 mL dry DMF. Yield after purification by RP-HPLC: 720 mg (88%).

Workup

  1. customYield
  2. customafter purification by RP-HPLC

Sources & evidence

ORD record
ord-4685ea90eb3447cd975723e3181564dd
Source dataset
uspto-grants-2014_12
Patent number
US08916548B2

Reaction notes

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