2-Penten-4-yn-1-ol → (2E)-5-(5-amino-6-phenoxypyrimidin-4-yl)-2-penten-4-yn-1-ol

HRID 1925963Notes

Reaction equation

HRID 1925963 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.[CH2:16]([OH:21])[CH:17]=[CH:18][C:19]#[CH:20]>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>[NH2:8][C:7]1[C:2]([C:20]#[C:19]/[CH:18]=[CH:17]/[CH2:16][OH:21])=[N:3][CH:4]=[N:5][C:6]=1[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 2

HCID 977582-Penten-4-yn-1-olHCID 860847854-Iodo-6-phenoxy-5-pyrimidinamine

Product 1

HCID 86615752(2E)-5-(5-amino-6-phenoxypyrimidin-4-yl)-2-penten-4-yn-1-olYield 59.9%

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 (3.5 g) was dissolved in a mixed solvent of acetonitrile (185 mL)/triethylamine (136 mL), and 2-penten-4-yn-1-ol (1.1 g), trans-dichlorobis(triphenylphosphine)palladium(II) (392 mg) and copper(I) iodide (127 mg) were sequentially added. The title compound (1.79 g) was obtained as a powder by the reaction in the same manner as in Example 9 (iv).

Workup

  1. additionwere sequentially added

Sources & evidence

ORD record
ord-9ff0f00dd04349e68537780a3fd844b4
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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