Triethylamine → HCID 58513250, compound

HRID 1405022Notes

Reaction equation

HRID 1405022 reaction equation
[Cl:1][C:2]1[C:7](I)=[C:6]([CH3:9])[N:5]=[C:4]([NH2:10])[N:3]=1.[CH3:11][Si:12]([C:15]#[CH:16])([CH3:14])[CH3:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.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:16]#[C:15][Si:12]([CH3:14])([CH3:13])[CH3:11])=[C:6]([CH3:9])[N:5]=[C:4]([NH2:10])[N:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 116447204-Chloro-5-iodo-6-methylpyrimidin-2-amine

Product 1

HCID 58513250HCID 58513250, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

The title compound is synthesized according to general procedure GP2 starting from 5.0 g (19 mmol) 4-chloro-5-iodo-6-methyl-pyrimidin-2-ylamine (GP3) and 3.6 mL (26 mmol) trimethylsilylethyne using 352 mg (1.9 mmol) CuI, 485 mg triphenylphosphine (1.9 mmol), 1.3 g (1.9 mmol) PdCl2(PPh3)2 and 26 mL (185 mmol) triethylamine in 100 mL dry DMF. For the work-up the solvent is removed in vacuo and the product is purified by RP-MPLC (ACN/H2O gradient). Yield: 1.6 g (38%).

Workup

  1. customFor the work-up the solvent is removed in vacuo
  2. customthe product is purified by RP-MPLC (ACN/H2O gradient)

Sources & evidence

ORD record
ord-0c63cc971ce8452a838ae92c2f7851a7
Source dataset
uspto-grants-2014_12
Patent number
US08916548B2

Reaction notes

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