Triethylamine → HCID 58513216, compound

HRID 1405018Notes

Reaction equation

HRID 1405018 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:18]=[CH:17][CH:16]=[CH:15][N:14]=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:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[C:6]([CH3:9])[N:5]=[C:4]([NH2:10])[N:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 137268EthynylpyridineHCID 116447204-Chloro-5-iodo-6-methylpyrimidin-2-amine

Product 1

HCID 58513216HCID 58513216, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

The title compound is synthesized according to general procedure GP2 starting from 1.5 g (5.6 mmol) 4-chloro-5-iodo-6-methyl-pyrimidin-2-ylamine (GP3) and 0.84 mL (8.4 mmol) 2-ethynyl-pyridine using 106 mg (0.57 mmol) CuI, 390 mg (0.56 mmol) PdCl2(PPh3)2 and 7.8 mL (56 mmol) triethylamine in 10 mL dry DMF. Additional amounts are added after 24 h and 48 h reaction time, respectively. For the work-up the solvent is removed in vacuo and the product is purified by chromatography on silica gel using a DCM/MeOH gradient. Yield: 2.0 g (>100%, approximately 70% pure).

Workup

  1. additionAdditional amounts are added after 24 h and 48 h
  2. customreaction time
  3. customFor the work-up the solvent is removed in vacuo
  4. customthe product is purified by chromatography on silica gel using a DCM/MeOH gradient

Sources & evidence

ORD record
ord-c8558603dad641778d5fa9c7d6ae810a
Source dataset
uspto-grants-2014_12
Patent number
US08916548B2

Reaction notes

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