1,2-Dichloroethane → HCID 89580281, compound

HRID 2276805Notes

Reaction equation

HRID 2276805 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[N:18]=[C:17]([C:19]([OH:21])=[O:20])[CH:16]=[C:15]([CH:22]=[CH2:23])[N:14]=3)=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[CH:26]1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CO>ClCCl>[F:1][C:2]1[CH:25]=[CH:24][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([C:13]3[N:18]=[C:17]([C:19]([O:21][CH3:26])=[O:20])[CH:16]=[C:15]([CH:22]=[CH2:23])[N:14]=3)=[CH:11][CH:12]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 887MethanolHCID 757711-HydroxybenzotriazoleHCID 89580074HCID 89580074, compound

Product 1

HCID 89580281HCID 89580281, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(4-(4-fluorophenoxy)phenyl)-6-vinylpyrimidine-4-carboxylic acid (23) (580 mg, 1.73 mmol), HOBt (279.5 mg, 2.07 mmol), and EDC (395.4 mg, 2.07 mmol) in dry dichloromethane were stirred for 20 minutes at room temperature and MeOH (3.46 mL, 86.5 mmol) was added thereto. After the reaction was complete, the solvent was removed in vacuo. The residue was dissolved in dichloromethane which was then washed with H2O. The organic layer was dried over anhydrous MgSO4 and concentrated to give oily residue. The resulting oil was purified by Combiflash (50% EtOAc in Hexanes) to give methyl 2-(4-(4-fluorophenoxy)phenyl)-6-vinylpyrimidine-4-carboxylate (24) (568 mg, 94% yield). 1H NMR (400 MHz, CD3OD): 8.45 (2H, d, J=8.5 Hz), 7.74 (1H, s), 6.90-7.01 (6H, m), 6.77-6.86 (1H, dd, J=11, 18 Hz), 6.60 (1H, d, J=17 Hz), 5.7 (1H, d, J=10.5 Hz), 3.98 (3H, s); LC/MS: m/z=351[M+H]+.

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane which
  3. washwas then washed with H2O
  4. dry with materialThe organic layer was dried over anhydrous MgSO4
  5. concentrationconcentrated
  6. customto give oily residue
  7. customThe resulting oil was purified by Combiflash (50% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-4ed8b672c6ea42a6921a271f28927b4d
Source dataset
uspto-grants-2015_09
Patent number
US09133131B2

Reaction notes

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