Triethylamine → HCID 58513524, compound

HRID 1405019Notes

Reaction equation

HRID 1405019 reaction equation
[Cl:1][C:2]1[C:7](I)=[C:6]([CH3:9])[N:5]=[C:4]([NH2:10])[N:3]=1.[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.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[C:7]([C:12]#[C:11][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)=[C:6]([CH3:9])[N:5]=[C:4]([NH2:10])[N:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 1860033-EthynylpyridineHCID 116447204-Chloro-5-iodo-6-methylpyrimidin-2-amine

Product 1

HCID 58513524HCID 58513524, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

The title compound is synthesized according to general procedure GP2 starting from 4.0 g (15 mmol) 4-chloro-5-iodo-6-methyl-pyrimidin-2-ylamine (GP3) and 2.0 g (19 mmol) 3-ethynyl-pyridine using 282 mg (1.5 mmol) CuI, 1.0 g (1.5 mmol) PdCl2(PPh3)2 and 21 mL (148 mmol) triethylamine in 200 mL dry DMF. For the work-up the reaction mixture is concentrated in vacuo before water is added. The precipitate is collected, dried at 40° C. and crystallized from MeOH/H2O. Yield: 3.0 g (83%).

Workup

  1. concentrationFor the work-up the reaction mixture is concentrated in vacuo before water
  2. additionis added
  3. customThe precipitate is collected
  4. customdried at 40° C.
  5. customcrystallized from MeOH/H2O

Sources & evidence

ORD record
ord-fd82339a7072408c8a8ca16cd016e610
Source dataset
uspto-grants-2014_12
Patent number
US08916548B2

Reaction notes

Loading…