Triethylamine → Tert-butyl (5-(4-chloro-2-((4-cyanophenyl)amino)pyrimidin-5-yl)-4-pentyn-1-yl)carbamate

HRID 2284817Notes

Reaction equation

HRID 2284817 reaction equation
[Cl:1][C:2]1[C:7](I)=[CH:6][N:5]=[C:4]([NH:9][C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)[N:3]=1.[C:18]([O:22][C:23](=[O:30])[NH:24][CH2:25][CH2:26][CH2:27][C:28]#[CH:29])([CH3:21])([CH3:20])[CH3:19].C(N(CC)CC)C.[Cl-].[NH4+]>CN(C)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.[Cu]I.C(OCC)(=O)C>[Cl:1][C:2]1[C:7]([C:29]#[C:28][CH2:27][CH2:26][CH2:25][NH:24][C:23](=[O:30])[O:22][C:18]([CH3:20])([CH3:19])[CH3:21])=[CH:6][N:5]=[C:4]([NH:9][C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)[N:3]=1

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 22904935tert-butyl N-(pent-4-yn-1-yl)carbamateHCID 900517824-((4-Chloro-5-iodopyrimidin-2-yl)amino)benzonitrile

Product 1

HCID 90052206Tert-butyl (5-(4-chloro-2-((4-cyanophenyl)amino)pyrimidin-5-yl)-4-pentyn-1-yl)carbamateYield 63.2%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-((4-chloro-5-iodopyrimidin-2-yl)amino)benzonitrile (J12, 100 mg) and tert-butyl(4-pentynyl)carbamate (77 mg) in N,N-dimethylformamide (3 mL), bis(triphenylphosphine)palladium(II) dichloride (20 mg), triethylamine (195 μL) and copper(I) iodide (11 mg) were added at room temperature, and the mixture was stirred at the same temperature for 1 hour. To the reaction mixture, saturated aqueous ammonium chloride and ethyl acetate were added. The organic layer was separated, washed with saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained solid matter was washed with a mixture of hexane and ethyl acetate (5:1), and then air-dried to obtain tert-butyl (5-(4-chloro-2-((4-cyanophenyl)amino)pyrimidin-5-yl)-4-pentyn-1-yl)carbamate (T5, 73 mg) as pale yellow solid.

Workup

  1. customThe organic layer was separated
  2. washwashed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. washThe obtained solid matter was washed with a mixture of hexane and ethyl acetate (5:1)
  6. customair-dried

Sources & evidence

ORD record
ord-fcf096da549b4ab2b040a00cc52af020
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

Loading…