Triethylamine → HCID 58513517, compound

HRID 1405034Notes

Reaction equation

HRID 1405034 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]=[C:15]([OH:19])[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>[NH2:8][C:6]1[N:5]=[C:4]([NH2:9])[C:3]([C:12]#[C:11][C:13]2[CH:14]=[C:15]([OH:19])[CH:16]=[CH:17][CH:18]=2)=[C:2]([Cl:1])[N:7]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 139144m-EthynylphenolHCID 58513369HCID 58513369, compound

Product 1

HCID 58513517HCID 58513517, 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 500 mg (1.8 mmol) 6-chloro-5-iodo-pyrimidine-2,4-diamine, 827 mg (7.0 mmol) 3-ethynyl-phenol, 35 mg (0.19 mmol) CuI, 129 mg (0.19 mmol) PdCl2(PPh3)2 and 4.1 mL triethylamine in 4 mL dry DMF. Yield after purification by RP-HPLC: 511 mg (100%).

Workup

  1. customYield
  2. customafter purification by RP-HPLC

Sources & evidence

ORD record
ord-ed5a48a98d634547b014c9a6e9e1d052
Source dataset
uspto-grants-2014_12
Patent number
US08916548B2

Reaction notes

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