Boron tribromide → 3-({5-Chloro-4-[(3-hydroxybenzyl)amino]pyrimidin-2-yl}amino)phenol

HRID 1614944Notes

Reaction equation

HRID 1614944 reaction equation
[Cl:1][C:2]1[C:3]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25]C)[CH:20]=2)=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15]C)[CH:10]=2)=[N:6][CH:7]=1.B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[C:3]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([OH:25])[CH:20]=2)=[N:4][C:5]([NH:8][C:9]2[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 584678475-Chloro-N(4)-(3-methoxybenzyl)-N(2)-(3-methoxyphenyl)pyrimidine-2,4-diamine

Product 1

HCID 584678453-({5-Chloro-4-[(3-hydroxybenzyl)amino]pyrimidin-2-yl}amino)phenolYield 58.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Into a 1-neck round-bottom flask were added 5-chloro-N(4)-(3-methoxybenzyl)-N(2)-(3-methoxyphenyl)pyrimidine-2,4-diamine (90 mg, 0.2 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 a dry ice bath 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 to give the desired product (40 mg, 50%). LCMS for C17H16ClN4O2 (M+H)+: m/z=343.0.

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

Sources & evidence

ORD record
ord-0f64242667f744029fd4af9aa5c881a1
Source dataset
uspto-grants-2014_07
Patent number
US08765727B2

Reaction notes

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