Sodium hydride → HCID 178518417, compound

HRID 750806Notes

Reaction equation

HRID 750806 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH2:5][OH:6].[H-].[Na+].CS([C:17]1[N:22]=[C:21]([OH:23])[C:20]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)=[C:19]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][C:32]=2[Cl:38])[N:18]=1)(=O)=O>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH2:5][O:6][C:17]1[N:22]=[C:21]([OH:23])[C:20]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)=[C:19]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][C:32]=2[Cl:38])[N:18]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 5228333,4-Difluorobenzyl alcoholHCID 178504853HCID 178504853, compound

Product 1

HCID 178518417HCID 178518417, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a round bottom flask fitted with a magnetic stir bar and rubber septum was added 2 mL DMF, 3,4-difluorobenzyl alcohol (14 μl, 0.11 mmol) and sodium hydride (60% in oil, 4.5 mg, 0.12 mmol). The flask was flushed with nitrogen and 2-methylsulfonyl-4-hydroxy-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine (from Step A) (43 mg, 0.1 mmol) in 500 μL DMF was added by syringe. After 1 h, the reaction was quenched with aqueous NH4Cl. A precipitate fell out of solution and it was filtered, washed with water and dried under reduced pressure. HPLC/MS: m/e=494 (M+); Rt=4.28 min; 1H-NMR 500 MHz (CDCl3): δ 5.39 (s, 2H), 7.04 (d, J=9 Hz, 2H), 7.09 (d, J=9 Hz, 2H), 7.15-7.22 (m, 4H), 7.22-7.28 (m, 1H), 7.41 (d, J=2 Hz, 1H).

Workup

  1. customTo a round bottom flask fitted with a magnetic stir bar
  2. additionwas added by syringe
  3. customthe reaction was quenched with aqueous NH4Cl
  4. filtrationwas filtered
  5. washwashed with water
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-2b29139e20e74d1ab0e9f4a651bd9c7f
Source dataset
uspto-grants-2008_07
Patent number
US07405221B2

Reaction notes

Loading…