Pyridine → HCID 60004112, compound

HRID 2183464Notes

Reaction equation

HRID 2183464 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[CH:11]=1)[CH3:9])(C)(C)C.Br[C:19]1[CH:20]=[N:21][CH:22]=[N:23][CH:24]=1.C(=O)([O-])[O-].[K+].[K+].N1C=CC=CC=1>[Cu](I)I.CCOC(C)=O.C(Cl)Cl>[N:21]1[CH:20]=[C:19]([O:16][C:12]2[CH:11]=[C:10]([C@@H:8]([NH2:7])[CH3:9])[CH:15]=[CH:14][CH:13]=2)[CH:24]=[N:23][CH:22]=1

Participants

8

Reactant 4

HCID 1049PyridineHCID 11430Potassium CarbonateHCID 783445-BromopyrimidineHCID 56971802Tert-butyl [(1S)-1-(3-hydroxyphenyl)ethyl]carbamate

Product 1

HCID 60004112HCID 60004112, compoundYield 89.6%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of (S)-[1-(3-hydroxy-phenyl)-ethyl]-carbamic acid tert-butyl ester (1 g, 4.2 mmol), 5-bromo-pyrimidine (0.8 g, 5.1 mmol), potassium carbonate (powder, 1.4 g, 10.1 mmol), copper iodide (325 mesh powder, 0.6 g, 3.2 mmol) and pyridine (5 mL) was heated at 115° C. for 24 h. CH2Cl2 (100 mL) was added, the reaction mixture was filtered through celite, rinsed with CH2Cl2 (2×50 mL), and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with 1:1/Hexane:EtOAc to give the title product (0.81 g, 61% yield).

Workup

  1. filtrationthe reaction mixture was filtered through celite
  2. washrinsed with CH2Cl2 (2×50 mL)
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by flash column chromatography on silica gel eluting with 1:1/Hexane

Sources & evidence

ORD record
ord-76947cb7044f444ebb8c566b9a136d1b
Source dataset
uspto-grants-2005_05
Patent number
US06900210B2

Reaction notes

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