Dimethylformamide → HCID 59643065, compound

HRID 2251076Notes

Reaction equation

HRID 2251076 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[NH:9][C:10]1[C:15]([CH:16]=O)=[CH:14][N:13]=[C:12]([S:18][CH3:19])[N:11]=1.BrCC([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[F:30])=O.[C:31](=[O:34])([O-])[O-].[K+].[K+].[CH3:37]N(C=O)C>CCOC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:10]2[N:11]=[C:12]([S:18][CH3:19])[N:13]=[CH:14][C:15]=2[CH:16]=[C:37]1[C:31]([C:28]1[CH:27]=[CH:26][C:25]([F:30])=[CH:24][CH:29]=1)=[O:34]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 27374492-Bromo-2'-fluoroacetophenoneHCID 59643083HCID 59643083, compound

Product 1

HCID 59643065HCID 59643065, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(2,6-difluoro-phenylamino)-2-methylsulfanyl-pyrimidine-5-carbaldehyde, 2, (5.4 g, 8.3 mmol) in DMF (107 mL) is added 2-bromo-1-(2-fluorophenyl)-ethanone (2.7 g, 12.5 mmol) and potassium carbonate (8.0 g, 57.7 mmol). The reaction mixture is stirred at room temp for 18 hours then diluted with EtOAc and washed with aqueous saturated NH4Cl three times. The organic phase is washed with aqueous saturated NaHCO3 and brine, dried (MgSO4), filtered and concentrated in vacuo. The resulting residue is purified over silica (10% EtOAc//hexanes) to afford 4.6 g of the desired product as a purple solid: 1H NMR (300 MHz, CDCl3) δ 8.98 (s, 1H), 8.00 (dd, J=5.4, 3.4 Hz, 2H), 7.50-7.40 (m, 1H), 7.25-7.05 (m, 5H), 2.52 (s, 3H); ESI+ MS: m/z (rel intensity) 400.1 (100, M++H).

Workup

  1. washwashed with aqueous saturated NH4Cl three times
  2. washThe organic phase is washed with aqueous saturated NaHCO3 and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue is purified over silica (10% EtOAc//hexanes)

Sources & evidence

ORD record
ord-be195632cc6f4e0790b233b2b8248646
Source dataset
uspto-grants-2008_01
Patent number
US07319102B1

Reaction notes

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