4-Iodo-2-(methylthio)pyrimidine → N-{1-Methyl-2-[4-(2-methylsulfanyl-pyrimidin-4-ylethynyl)-phenyl]-ethyl}acetamide

HRID 76193Notes

Reaction equation

HRID 76193 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]([NH:12][C:13](=[O:15])[CH3:14])[CH3:11])=[CH:5][CH:4]=1)#[CH:2].I[C:17]1[CH:22]=[CH:21][N:20]=[C:19]([S:23][CH3:24])[N:18]=1>C(N)(CC)C.O.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>[CH3:11][CH:10]([NH:12][C:13](=[O:15])[CH3:14])[CH2:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[C:2][C:17]2[CH:22]=[CH:21][N:20]=[C:19]([S:23][CH3:24])[N:18]=2)=[CH:4][CH:5]=1

Participants

6

Reactant 2

HCID 38589014-Iodo-2-(methylthio)pyrimidineHCID 86669621N-(1-(4-ethynylphenyl)propan-2-yl)acetamide

Product 1

HCID 66611369N-{1-Methyl-2-[4-(2-methylsulfanyl-pyrimidin-4-ylethynyl)-phenyl]-ethyl}acetamide

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent2×HCID 24874Sec-ButylamineSolvent

Procedure

To 0.52 g (2.58 mmol) N-[2-(4-ethynyl-phenyl)-1-methyl-ethyl]-acetamide (I58.3) and 0.50 g (1.98 mmol) 4-iodo-2-(methylthio)pyrimidine in 3 mL sec-butylamine and 3 mL water are added 0.14 g (0.20 mmol) bis(triphenylphosphine)dichloro-palladium and the mixture is stirred at r.t. over night. The reaction mixture is diluted with water and extracted with DCM. The organic layer is dried with Na2SO4 and the solvent is removed in vacuo. The residue is purified by column chromatography (silica gel, DCM/MeOH 96/4). The resulting product is triturated with diethylether.

Workup

  1. extractionextracted with DCM
  2. dry with materialThe organic layer is dried with Na2SO4
  3. customthe solvent is removed in vacuo
  4. customThe residue is purified by column chromatography (silica gel, DCM/MeOH 96/4)
  5. customThe resulting product is triturated with diethylether

Sources & evidence

ORD record
ord-81d7551219d24e2784d8aa15c266cd1c
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Reaction notes

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