Dichloromethane → HCID 131735900, compound

HRID 2207387Notes

Reaction equation

HRID 2207387 reaction equation
ClCCl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:23][C:24]1[CH:25]=[C:26]([C:41]2[CH:42]=[CH:43][C:44]([CH2:47]O)=[N:45][CH:46]=2)[CH:27]=[C:28]([NH:30][C:31]2[N:36]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:34]=[CH:33][N:32]=2)[CH:29]=1.C(Br)(Br)(Br)[Br:50]>S([O-])([O-])(=O)=S.[Na+].[Na+]>[Br:50][CH2:47][C:44]1[N:45]=[CH:46][C:41]([C:26]2[CH:27]=[C:28]([NH:30][C:31]3[N:36]=[C:35]([C:37]([F:38])([F:40])[F:39])[CH:34]=[CH:33][N:32]=3)[CH:29]=[C:24]([CH3:23])[CH:25]=2)=[CH:42][CH:43]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 131735901HCID 131735901, compound

Product 1

HCID 131735900HCID 131735900, compound

Reagents, catalysts & solvents 1

HCID 24477Sodium ThiosulfateSolvent

Procedure

Dichloromethane (3.24 mL) and triphenylphosphine (0.459 g, 1.75 mmol) was added to [5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-2-yl]methanol (0.35 g, 0.971 mmol). Carbon tetrabromide (0.451 g, 1.36 mmol) was added slowly to the reaction mixture and stirred for 8 hours at room temperature. The reaction mixture was diluted with 10% sodium thiosulfate (5.00 mL) and the organic layer was separated, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/hexanes) to yield N-{3-[6-(bromomethyl)pyridin-3-yl]-5-methylphenyl}-4-(trifluoromethyl)pyrimidin-2-amine. MS APCI calc'd for C18H15BrF3N4 [M+H]+ 423 and 425. found 423 and 425.

Workup

  1. customthe organic layer was separated
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel chromatography (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-b5b4496caa164c789c34eed35cad68b3
Source dataset
uspto-grants-2016_06
Patent number
US09376418B2

Reaction notes

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