Water → HCID 59526076, compound

HRID 386092Notes

Reaction equation

HRID 386092 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][OH:9])[N:3]=1.[CH3:10][N:11]=[C:12]=[O:13].O>CN(C=O)C.[Cu]Cl>[CH3:10][NH:11][C:12](=[O:13])[O:9][CH2:8][C:4]1[N:3]=[C:2]([Cl:1])[CH:7]=[CH:6][N:5]=1

Participants

6

Reactant 3

HCID 962WaterHCID 12228Methyl IsocyanateHCID 55273715(4-Chloropyrimidin-2-yl)methanol

Product 1

HCID 59526076HCID 59526076, compound

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 6228DimethylformamideSolvent

Procedure

(4-Chloropyrimidin-2-yl)methanol (Example 548, Step 1) (0.304 g, 2.10 mmol) and copper(I) chloride (0.208 g, 2.10 mmol) were taken up in DMF (10 mL) and stirred at room temperature for 5 minutes. Methyl isocyanate (0.120 g, 2.10 mmol) was added and stirring at room temperature continued for 3 hours. Water was added and the reaction mixture was extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. Purification of the residue by silica gel chromatography (12-100% EtOAc-hexanes) gave the title compound as a white solid.

Workup

  1. stirringstirring at room temperature
  2. waitcontinued for 3 hours
  3. extractionthe reaction mixture was extracted with EtOAc (2×)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification of the residue by silica gel chromatography (12-100% EtOAc-hexanes)

Sources & evidence

ORD record
ord-1439867f8d8e4e919db755f93c73eecb
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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