4-Iodo-6-phenoxy-5-pyrimidinamine → 3-(5-Amino-6-phenoxypyrimidin-4-yl)-2-propyn-1-ol

HRID 1925962Notes

Reaction equation

HRID 1925962 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(#N)C.C(N(CC)CC)C.C(O)C#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:2]#[C:7][CH2:6][OH:9])=[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 1

HCID 860847854-Iodo-6-phenoxy-5-pyrimidinamine

Product 1

HCID 675212843-(5-Amino-6-phenoxypyrimidin-4-yl)-2-propyn-1-olYield 174.8%

Reagents, catalysts & solvents 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolventHCID 7859Propargyl alcoholSolventHCID 8471TriethylamineSolvent

Procedure

4-Iodo-6-phenoxypyrimidin-5-amine (3.0 g) was dissolved in a mixed solvent of acetonitrile (159 mL)/triethylamine (117 mL), and 2-propyn-1-ol (0.669 mL), trans-dichlorobis(triphenylphosphine)palladium(II) (336 mg) and copper(I) iodide (109.5 mg) were sequentially added. The title compound (2.02 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-4e8871c64922422e80b5786f79331acb
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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