2-Chloro-5-iodopyrimidine → N-(1-(4-((2-(sec-Butylamino)pyrimidin-5-yl)ethynyl)phenyl)propan-2-yl)acetamide

HRID 76194Notes

Reaction equation

HRID 76194 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].Cl[C:17]1[N:22]=[CH:21][C:20](I)=[CH:19][N:18]=1>O.C(N)(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>[CH:10]([NH:12][C:17]1[N:22]=[CH:21][C:20]([C:2]#[C:1][C:3]2[CH:8]=[CH:7][C:6]([CH2:9][CH:10]([NH:12][C:13](=[O:15])[CH3:14])[CH3:11])=[CH:5][CH:4]=2)=[CH:19][N:18]=1)([CH2:9][CH3:6])[CH3:11]

Participants

6

Reactant 2

HCID 17142232-Chloro-5-iodopyrimidineHCID 86669621N-(1-(4-ethynylphenyl)propan-2-yl)acetamide

Product 1

HCID 66614337N-(1-(4-((2-(sec-Butylamino)pyrimidin-5-yl)ethynyl)phenyl)propan-2-yl)acetamide

Reagents, catalysts & solvents 3

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

Procedure

2.50 g (12.4 mmol) N-(1-(4-ethynylphenyl)propan-2-yl)acetamide (I58.3), 3.0 g (12.42 mmol) 2-chloro-5-iodopyrimidine and 872 mg (1.24 mmol) bis(triphenylphosphine)dichloropalladium in 10 mL water and 10 mL sec-butylamine are 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 98/2).

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 98/2)

Sources & evidence

ORD record
ord-609f1d94c0cb4b319438f366e142855c
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Reaction notes

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