Water → HCID 58513427, compound

HRID 1405020Notes

Reaction equation

HRID 1405020 reaction equation
[Cl:1][C:2]1[C:7](I)=[C:6]([CH3:9])[N:5]=[C:4]([NH2:10])[N:3]=1.[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]#[CH:19])=[CH:14][N:13]=1.C(N(CC)CC)C.O>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>[NH2:11][C:12]1[N:13]=[CH:14][C:15]([C:18]#[C:19][C:7]2[C:2]([Cl:1])=[N:3][C:4]([NH2:10])=[N:5][C:6]=2[CH3:9])=[CH:16][CH:17]=1

Participants

8

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 116447204-Chloro-5-iodo-6-methylpyrimidin-2-amineHCID 219548275-Ethynylpyridin-2-amine

Product 1

HCID 58513427HCID 58513427, 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 1.5 g (5.7 mmol) 4-chloro-5-iodo-6-methyl-pyrimidin-2-ylamine (GP3) and 1.7 g (15 mmol) 2-amino-5-ethynyl-pyridine (GP15) using 106 mg (0.56 mmol) CuI, 390 mg (0.56 mmol) PdCl2(PPh3)2 and 8 mL (55 mmol) triethylamine in 12 mL dry DMF. For the work-up water is added to the reaction mixture. The precipitate is collected, dried at 40° C. and re-crystallized from MeOH. Yield: 1.5 g (83%, approximately 80% pure).

Workup

  1. customThe precipitate is collected
  2. customdried at 40° C.
  3. customre-crystallized from MeOH

Sources & evidence

ORD record
ord-3f71b38fa8b940768f6e64fe0e63cef2
Source dataset
uspto-grants-2014_12
Patent number
US08916548B2

Reaction notes

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