Potassium Carbonate → HCID 58337657, compound

HRID 1887439Notes

Reaction equation

HRID 1887439 reaction equation
[Br:1][C:2]1[CH:7]=[C:6](F)[CH:5]=[C:4]([Cl:9])[CH:3]=1.[OH:10][C:11]1[CH:12]=[N:13][CH:14]=[N:15][CH:16]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([Cl:9])[CH:3]=1)[O:10][C:11]1[CH:12]=[N:13][CH:14]=[N:15][CH:16]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 565855Pyrimidin-5-olHCID 27362231-Bromo-3-chloro-5-fluorobenzene

Product 1

HCID 58337657HCID 58337657, compoundYield 53.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Bromo-3-chloro-5-fluorobenzene (1.0 g, 4.8 mmol, 1.0 eq), 5-hydroxypyrimidine (454 mg, 5.02 mmol, 1.05 eq), K2CO3 (792 mg, 5.73 mmol, 1.20 eq) and DMF (15 mL) were added to a microwave vial and microwaved at 200° C. for 30 minutes. The reaction was filtered and concentrated on silica gel (5 g). The silica gel was loaded on top a fresh bed of silica gel and washed with 50% ethyl acetate/hexane. The solvents were removed in vacuo and the crude mixture was purified by flash chromatography on silica gel afforded 735 mg (43%) of the title compound as a golden oil: 1H NMR (400 MHz, DMSO-d6) δ 9.07 (s, 1H), 8.73 (s, 2H), 7.58 (t, J=1.7 Hz, 1H), 7.43 (t, J=1.9 Hz, 1H), 7.35 (t, J=2.0 Hz, 1H); ES-MS [M+1]+: 285.0.

Workup

  1. custommicrowaved at 200° C. for 30 minutes
  2. filtrationThe reaction was filtered
  3. concentrationconcentrated on silica gel (5 g)
  4. washwashed with 50% ethyl acetate/hexane
  5. customThe solvents were removed in vacuo
  6. customthe crude mixture was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-fb27fc8b7da542ec874d9e784add969e
Source dataset
uspto-grants-2013_08
Patent number
US08501757B2

Reaction notes

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