Water → HCID 71150046, compound

HRID 1853447Notes

Reaction equation

HRID 1853447 reaction equation
Br[C:2]1[CH:17]=[CH:16][C:5]([CH2:6][CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH3:24][O:25][C:26]1[N:31]=[C:30]([O:32][CH3:33])[C:29](B(O)O)=[CH:28][N:27]=1.O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C.CCCCCC.C(OCC)(=O)C>[CH3:24][O:25][C:26]1[N:31]=[C:30]([O:32][CH3:33])[C:29]([C:2]2[CH:17]=[CH:16][C:5]([CH2:6][CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][CH:3]=2)=[CH:28][N:27]=1

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2736209(2,4-Dimethoxypyrimidin-5-yl)boronic acidHCID 14221818[2-(4-Bromo-phenyl)ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 71150046HCID 71150046, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
90 °C

Procedure

Industrial methylated spirits (IMS; 15 mL) and water (5 mL) were degassed thoroughly. tert-butyl 4-bromophenethylcarbamate (1.08 g, 3.63 mmol), sodium carbonate (1.54 g, 14.52 mmol), palladium tetrakis (0.42 g, 0.36 mmol) and 2,4-dimethoxy-5-pyrimidinylboronic acid (1.00 g, 5.44 mmol) were added and the reaction mixture heated to 90° C. for 18 hours. No starting material was observed by LCMS. Water (100 ml) and ethyl acetate (300 ml) were added and the organic layer separated. The organic layer was washed with water (100 ml), dried (MgSO4) and concentrated to give a yellow oil. The crude residue was subject to column chromatography (20 to 60% ethyl acetate/hexane) to give a yellow oil, tert-butyl 4-(2,4-dimethoxypyrimidin-5-yl)phenethylcarbamate, which crystallized on standing (1.18 g, 3.28 mmol, 91%).

Workup

  1. customIndustrial methylated spirits (IMS; 15 mL) and water (5 mL) were degassed thoroughly
  2. customthe organic layer separated
  3. washThe organic layer was washed with water (100 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customto give a yellow oil

Sources & evidence

ORD record
ord-b9a2e73a9e774f40b338ea2048fe49ba
Source dataset
uspto-grants-2015_02
Patent number
US08962646B2

Reaction notes

Loading…