4-(3-Benzyloxy-propyl)-6-trimethylstannanyl-pyrimidine-2-carbonitrile → 4-(3-Benzyloxy-propyl)-6-(3-methanesulfonylamino-5-trifluoromethylphenyl)-pyrimidine-2-carbonitrile

HRID 733187Notes

Reaction equation

HRID 733187 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[CH2:17]([O:24][CH2:25][CH2:26][CH2:27][C:28]1[CH:33]=[C:32]([Sn](C)(C)C)[N:31]=[C:30]([C:38]#[N:39])[N:29]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C=O)C.C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:17]([O:24][CH2:25][CH2:26][CH2:27][C:28]1[CH:33]=[C:32]([C:2]2[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH:3]=2)[N:31]=[C:30]([C:38]#[N:39])[N:29]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 2

HCID 578391104-(3-Benzyloxy-propyl)-6-trimethylstannanyl-pyrimidine-2-carbonitrileHCID 65491442N-(3-Bromo-5-(trifluoromethyl)phenyl)methanesulfonamide

Product 1

HCID 690455274-(3-Benzyloxy-propyl)-6-(3-methanesulfonylamino-5-trifluoromethylphenyl)-pyrimidine-2-carbonitrile

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-(3-Bromo-5-trifluoromethyl-phenyl)-methanesulfonamide (37 mg), 4-(3-benzyloxy-propyl)-6-trimethylstannanyl-pyrimidine-2-carbonitrile (40 mg) and dichlorobis(triphenylphosphine)palladium(II) (7 mg) in DMF (1 mL) were heated in a microwave to 180° C. for five minutes. The mixture was diluted with ethyl acetate (10 mL) and filtered through celite. The filtrate was washed with water (10 mL) and saturated sodium chloride solution (10 mL). Organics were separated, dried over sodium sulphate, filtered and solvent was removed under reduced pressure to yield crude product. Purification by HPLC afforded 4-(3-benzyloxy-propyl)-6-(3-methanesulfonylamino-5-trifluoromethylphenyl)-pyrimidine-2-carbonitrile.

Workup

  1. filtrationfiltered through celite
  2. washThe filtrate was washed with water (10 mL) and saturated sodium chloride solution (10 mL)
  3. customOrganics were separated
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customsolvent was removed under reduced pressure
  7. customto yield crude product
  8. customPurification by HPLC

Sources & evidence

ORD record
ord-673ce543b0e2442da4b369bd50a38d2e
Source dataset
uspto-grants-2009_09
Patent number
US07589095B2

Reaction notes

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