Water → 3-{(1S)-1-[(2-{[3-(Bromomethyl)phenyl]amino}-5-chloropyrimidin-4-yl)amino]ethyl}phenol

HRID 1614958Notes

Reaction equation

HRID 1614958 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.B(Br)(Br)[Br:29].O.CCOC(C)=O>C(Cl)Cl>[Br:29][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 962Water2×HCID 8857Ethyl AcetateHCID 25134Boron tribromideHCID 58467829{3-[(5-Chloro-4-{[(1S)-1-(3-methoxyphenyl)ethyl]amino}pyrimidin-2-yl)amino]phenyl}methanol

Product 1

HCID 584679193-{(1S)-1-[(2-{[3-(Bromomethyl)phenyl]amino}-5-chloropyrimidin-4-yl)amino]ethyl}phenolYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of {3-[(5-chloro-4-{[(1S)-1-(3-methoxyphenyl)ethyl]amino}pyrimidin-2-yl)amino]phenyl}methanol (0.30 g, 0.78 mmol) in methylene chloride (5.0 mL) was added slowly a solution of boron tribromide in methylene chloride (3.9 mL, 3.9 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 a dry ice bath when water was added. The mixture was allowed to warm up to rt. Water and EtOAc were added. The aqueous layer was extracted with EtOAc twice. The combined organic layers were dried over Na2SO4, filtered, and concentrated (then triturated with cold EtOAc) to give the desired product as a white powder (0.255 g, 75%). LCMS for C19H19BrClN4O (M+H)+: m/z=433.0, 435.0.

Workup

  1. additionwas added
  2. temperatureto warm up to rt
  3. extractionThe aqueous layer was extracted with EtOAc twice
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated (
  7. customthen triturated with cold EtOAc)

Sources & evidence

ORD record
ord-2a377260dc37468c9bc60caf6a4b81c1
Source dataset
uspto-grants-2014_07
Patent number
US08765727B2

Reaction notes

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