5-Bromopyrimidine → HCID 63894507, compound

HRID 879655Notes

Reaction equation

HRID 879655 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[N:6][CH:7]=1.C([Mg]Cl)(C)C.[Br:13][C:14]1[CH:15]=[CH:16][C:17]([F:22])=[C:18]([CH:21]=1)[CH:19]=[O:20]>C1COCC1>[Br:13][C:14]1[CH:15]=[CH:16][C:17]([F:22])=[C:18]([CH:19]([C:2]2[CH:3]=[N:4][CH:5]=[N:6][CH:7]=2)[OH:20])[CH:21]=1

Participants

5

Reactant 3

HCID 783445-BromopyrimidineHCID 7363275-Bromo-2-fluorobenzaldehydeHCID 178418918HCID 178418918, compound

Product 1

HCID 63894507HCID 63894507, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To an oven-dried flask was added anhydrous THF (40 mL) and 5-bromopyrimidine (6.36 g, 40 mmol). 2M isopropylmagnesium chloride in THF (22 mL) was then added dropwise over several minutes at 0° C. The mixture was stirred at 0° C. for 30 minutes, and then 5-bromo-2-fluorobenzaldehyde (2.4 mL, 20 mmol) was added. After warming to room temperature, the reaction was quenched with saturated aqueous NH4Cl. The aqueous layer was extracted with EtOAc, dried over MgSO4, and purified by column chromatography (gradient 0 to 60% EtOAc in hexanes) to afford the product. 1H NMR (400 MHz, CDCl3) δ 9.10 (s, 1H), 8.74 (s, 2H), 7.71 (dd, J=6.4, 2.5 Hz, 1H), 7.43 (ddd, J=8.7, 4.6, 2.6 Hz, 1H), 6.95 (dd, J=9.5, 8.9 Hz, 1H), 6.15 (s, 1H).

Workup

  1. temperatureAfter warming to room temperature
  2. customthe reaction was quenched with saturated aqueous NH4Cl
  3. extractionThe aqueous layer was extracted with EtOAc
  4. dry with materialdried over MgSO4
  5. custompurified by column chromatography (gradient 0 to 60% EtOAc in hexanes)
  6. customto afford the product

Sources & evidence

ORD record
ord-65ebe875f23a43f283178f929ef5efb3
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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