Dichloromethane → HCID 58467857, compound

HRID 1614942Notes

Reaction equation

HRID 1614942 reaction equation
[Cl:1][C:2]1[C:3]([NH:17][C@@H:18]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26]C)[CH:21]=2)[CH3:19])=[N:4][C:5]([NH:8][C:9]2[CH:10]=[C:11]([CH2:15]O)[CH:12]=[CH:13][CH:14]=2)=[N:6][CH:7]=1.C(Cl)Cl.B(Br)(Br)[Br:32].C([O-])(O)=O.[Na+]>C(=O)=O>[Br:32][CH2:15][C:11]1[CH:10]=[C:9]([NH:8][C:5]2[N:4]=[C:3]([NH:17][C@@H:18]([C:20]3[CH:21]=[C:22]([OH:26])[CH:23]=[CH:24][CH:25]=3)[CH3:19])[C:2]([Cl:1])=[CH:7][N:6]=2)[CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 6344Dichloromethane3×HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 58467880HCID 58467880, compound

Product 1

HCID 58467857HCID 58467857, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 280Carbon DioxideSolvent

Procedure

Into a 1-neck round-bottom flask were added {3-[(5-chloro-4-{[(1R)-1-(3-methoxyphenyl)ethyl]amino}pyrimidin-2-yl)amino]phenyl}methanol (0.26 g, 0.68 mmol) and methylene chloride (5 mL). To the mixture was added a solution of boron tribromide in methylene chloride (3.0 mL, 3.0 mmol, 1.0 M) at 0° C. The mixture was allowed to warm up to rt and stirred overnight. The resultant mixture was cooled in dry ice when NaHCO3 (saturated aqueous solution, 10 mL) was added. The mixture was allowed to warm up to rt and DCM was added. The aqueous layer was extracted with DCM twice. The organic layers were combined, dried, filtered, and concentrated under vacuum. The crude product was purified by silica gel column chromatography to give the desired product (40 mg, 30%). LCMS for C19H19BrClN4O (M+H)+: m/z=432.9, 434.9.

Workup

  1. additionwas added
  2. temperatureto warm up to rt
  3. extractionThe aqueous layer was extracted with DCM twice
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-15f65832269d4c228c3deb719ab20019
Source dataset
uspto-grants-2014_07
Patent number
US08765727B2

Reaction notes

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