Benzyl Alcohol → HCID 67960231, compound

HRID 536172Notes

Reaction equation

HRID 536172 reaction equation
[C:1]1([CH2:7][OH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[C:12]1[N:17]=[C:16]([O:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[C:30]([C:35]([F:38])([F:37])[F:36])[CH:29]=3)=[CH:23][CH:22]=2)[C:15]([F:39])=[CH:14][N:13]=1>CN(C)C=O>[Cl:34][C:31]1[CH:32]=[CH:33][C:28]([O:27][C:24]2[CH:23]=[CH:22][C:21]([CH2:20][CH2:19][O:18][C:16]3[C:15]([F:39])=[CH:14][N:13]=[C:12]([O:8][CH2:7][C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[N:17]=3)=[CH:26][CH:25]=2)=[CH:29][C:30]=1[C:35]([F:36])([F:38])[F:37]

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 86697027HCID 86697027, compound

Product 1

HCID 67960231HCID 67960231, compoundYield 73.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of phenylmethanol (100 μL, 0.965 mmol) in N,N-dimethylformamide (DMF) (8 mL) was added sodium hydride (232 mg, 5.79 mmol) 0° C., the 2-chloro-4-{[2-(4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}phenyl)ethyl]oxy}-5-fluoropyrimidine (432 mg, 0.965 mmol) was added at 0° C. after 10 min. The reaction mixture was stirred for 30 min, and poured into ice-water (100 mL), extracted with ethyl acetate (50 mL) twice. Combined organic parts were washed with water and brine, dried over sodium sulfate, filtered and concentrated. Purification via ISCO system afforded the title product (370 mg). LC-MS (ESI): m/z 519[M+H]+; 6.26 min (ret time).

Workup

  1. extractionextracted with ethyl acetate (50 mL) twice
  2. washCombined organic parts were washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification via ISCO system

Sources & evidence

ORD record
ord-b0c7286f3df5476bbcd797b347d554a2
Source dataset
uspto-grants-2014_10
Patent number
US08859573B2

Reaction notes

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