Acetic Acid → 2-[5-Bromo-2-(4-fluorophenyl)-1,3-oxazol-4-yl]pyrimidine

HRID 1469389Notes

Reaction equation

HRID 1469389 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[F:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[O:17][CH:18]=[C:19]([C:21]3[N:26]=[CH:25][CH:24]=[CH:23][N:22]=3)[N:20]=2)=[CH:12][CH:11]=1.C(O)(=O)C>ClCCl>[Br:8][C:18]1[O:17][C:16]([C:13]2[CH:14]=[CH:15][C:10]([F:9])=[CH:11][CH:12]=2)=[N:20][C:19]=1[C:21]1[N:26]=[CH:25][CH:24]=[CH:23][N:22]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 67184N-bromobutanimideHCID 894857232-[2-(4-Fluorophenyl)-1,3-oxazol-4-yl]pyrimidine

Product 1

HCID 894856732-[5-Bromo-2-(4-fluorophenyl)-1,3-oxazol-4-yl]pyrimidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

NBS (2.03 g, 11.4 mmol) and 2-[2-(4-fluorophenyl)-1,3-oxazol-4-yl]pyrimidine (1.4) (2.5 g, 10.36 mmol) in a solvent mixture of 1:1 acetic acid and dichloromethane were stirred at room temperature for 3 hr. Then the solvents were removed in vacuo, and the resulting residue was dissolved in EtOAc. The solution was washed with aqueous Na2S2O3 and brine, and dried over MgSO4. The drying agent was filtered off and the filtrate was concentrated to give the title compound. LC-MS m/z 321.96 [M+1]+.

Workup

  1. customThen the solvents were removed in vacuo
  2. dissolutionthe resulting residue was dissolved in EtOAc
  3. washThe solution was washed with aqueous Na2S2O3 and brine
  4. dry with materialdried over MgSO4
  5. filtrationThe drying agent was filtered off
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ec067a11c44545aca47d853930fb9a1c
Source dataset
uspto-grants-2015_04
Patent number
US09006268B2

Reaction notes

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