Methanol → HCID 86700258, compound

HRID 879449Notes

Reaction equation

HRID 879449 reaction equation
[NH:1]1[CH:9]=[C:7]([CH3:8])[C:5](=[O:6])[NH:4][C:2]1=[O:3].[Br:10][C:11]1[CH:12]=[C:13](B(O)O)[CH:14]=[CH:15][CH:16]=1.CO>O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C.O>[Br:10][C:11]1[CH:16]=[C:15]([N:1]2[CH:9]=[C:7]([CH3:8])[C:5](=[O:6])[NH:4][C:2]2=[O:3])[CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 1135ThymineHCID 2734318(3-Bromophenyl)boronic acid

Product 1

HCID 86700258HCID 86700258, compound

Reagents, catalysts & solvents 2

HCID 165397Cupric acetate monohydrateCatalystHCID 962WaterSolvent

Procedure

A 500 mL round bottom flask was charged with thymine (0.314 g, 2.49 mmol), 3-bromophenylboronic acid (1.00 g, 4.98 mmol), tetramethylethyldiamine (0.75 mL, 4.98 mmol), copper(II) acetate monohydrate (0.497 g, 2.49 mmol), methanol (200 mL), and H2O (50 mL). The blue reaction mixture was stirred for 48 h, concentrated and purified by CombiFlash (0 to 8% MeOH/CH2Cl2) to give desired product. LCMS-ESI+: calc'd for C11H9BrN2O2: 281.0 (M+H+); Found: 281.1 (M+H+).

Workup

  1. customThe blue reaction mixture
  2. concentrationconcentrated
  3. custompurified by CombiFlash (0 to 8% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-4036dbef186c4ec6ad06ba841ee96e81
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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