Water → HCID 58337756, compound

HRID 1887445Notes

Reaction equation

HRID 1887445 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1.Br[C:12]1[CH:13]=[N:14][CH:15]=[N:16][CH:17]=1.O>CN(C=O)C.C(OCC)(=O)C>[Br:3][C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[O:10][C:12]1[CH:13]=[N:14][CH:15]=[N:16][CH:17]=1

Participants

7

Reactant 4

HCID 962WaterHCID 115633-BromophenolHCID 24758Sodium hydrideHCID 783445-Bromopyrimidine

Product 1

HCID 58337756HCID 58337756, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

NaH (166 mg, 6.92 mmol, 1.10 eq) in DMF (15 mL) in a flame-dried microwave vial was cooled to 0° C. and 3-bromophenol (982 μL, 6.29 mmol, 1.00 eq) was added dropwise. The reaction was stirred for 30 min. at 0° C. at which point 5-bromopyrimidine (1.0 g, 6.3 mmol, 1.0 eq) was added and the reaction microwaved at 200° C. for 60 minutes. The reaction was diluted with ethyl acetate (50 mL) and was with water (3×). The organic layer was dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography on silica gel afforded 750 mg (52%) of the title compound as an orange oil: 1H NMR (400 MHz, CDCl3) δ 9.03 (s, 1H), 8.67 (s, 2H), 7.43-7.36 (m, 3H), 7.16 (dt, J=7.7, 1.9 Hz, 1H); ES-MS [M+1]+: 251.0.

Workup

  1. additionwas added
  2. customthe reaction microwaved at 200° C. for 60 minutes
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-3323e7b9c9974ce4a6c75e43890d4ef9
Source dataset
uspto-grants-2013_08
Patent number
US08501757B2

Reaction notes

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