Triethylamine → HCID 58513523, compound

HRID 1405024Notes

Reaction equation

HRID 1405024 reaction equation
I[C:2]1[C:3]([CH3:19])=[N:4][C:5]([NH2:18])=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=1.[CH3:20][Si:21]([C:24]#[CH:25])([CH3:23])[CH3:22].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>[CH3:17][S:14]([C:11]1[CH:12]=[CH:13][C:8]([C:7]2[C:2]([C:25]#[C:24][Si:21]([CH3:23])([CH3:22])[CH3:20])=[C:3]([CH3:19])[N:4]=[C:5]([NH2:18])[N:6]=2)=[CH:9][CH:10]=1)(=[O:16])=[O:15]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 58513304HCID 58513304, compound

Product 1

HCID 58513523HCID 58513523, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

The title compound is synthesized according to general procedure GP2 starting from 3.0 g (7.7 mmol) 5-iodo-4-methyl-6-(4-methanesulfonyl-phenyl)-pyrimidin-2-ylamine (A-33) and 1.6 mL (12 mmol) trimethylsilylethyne using 147 mg (0.77 mmol) CuI, 541 mg (0.77 mmol) PdCl2(PPh3)2 and 11 mL (7.7 mmol) triethylamine in 18 mL dry DMF. For the work-up the solvent is removed in vacuo and the product is purified by chromatography on silica (DCM/MeOH gradient). Yield: 2.45 g (71%, approximately 80% pure).

Workup

  1. customFor the work-up the solvent is removed in vacuo
  2. customthe product is purified by chromatography on silica (DCM/MeOH gradient)

Sources & evidence

ORD record
ord-96f34210bfc84993974d5aae7f2e98e3
Source dataset
uspto-grants-2014_12
Patent number
US08916548B2

Reaction notes

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