tert-butyl(dimethyl)[(2E)-2-penten-4-ynyloxy]silane → 4-((3E)-5-{[tert-butyl(dimethyl)silyl]oxy}-3-penten-1-ynyl)-6-phenoxypyrimidin-5-amine

HRID 1786869Notes

Reaction equation

HRID 1786869 reaction equation
I[C:2]1[C:7]([NH2:8])=[C:6]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:5]=[CH:4][N:3]=1.[C:16]([Si:20]([CH3:28])([CH3:27])[O:21][CH2:22]/[CH:23]=[CH:24]/[C:25]#[CH:26])([CH3:19])([CH3:18])[CH3:17]>C(#N)C.C(N(CC)CC)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.[Cu]I>[Si:20]([O:21][CH2:22]/[CH:23]=[CH:24]/[C:25]#[C:26][C:2]1[C:7]([NH2:8])=[C:6]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:5]=[CH:4][N:3]=1)([C:16]([CH3:17])([CH3:18])[CH3:19])([CH3:28])[CH3:27]

Participants

7

Reactant 2

HCID 10845580tert-butyl(dimethyl)[(2E)-2-penten-4-ynyloxy]silaneHCID 860847854-Iodo-6-phenoxy-5-pyrimidinamine

Product 1

HCID 866157514-((3E)-5-{[tert-butyl(dimethyl)silyl]oxy}-3-penten-1-ynyl)-6-phenoxypyrimidin-5-amineYield 87.8%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

4-Iodo-6-phenoxypyrimidin-5-amine (1.0 g) was dissolved in a mixed solvent of acetonitrile (53 mL)/triethylamine (39 mL), and tert-butyl(dimethyl)[(2E)-2-penten-4-ynyloxy]silane (753 mg), trans-dichlorobis(triphenylphosphine)palladium(II) (112 mg) and copper(I) iodide (36.5 mg) were sequentially added. The title compound (1.07 g) was obtained as crystals by the reaction in the same manner as in Example 9 (iv).

Workup

  1. additionwere sequentially added

Sources & evidence

ORD record
ord-ccbcaae9a5f940c3a8350c0dd2d6f435
Source dataset
uspto-grants-2009_03
Patent number
US07507740B2

Reaction notes

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