Sodium Carbonate → 4-Bromo-3-{[(2-{[3-(3-bromopropyl)phenyl]amino}-5-chloropyrimidin-4-yl)amino]methyl}phenol

HRID 1614970Notes

Reaction equation

HRID 1614970 reaction equation
[Br:1][C:2]1[CH:27]=[CH:26][C:25]([O:28]C)=[CH:24][C:3]=1[CH2:4][NH:5][C:6]1[C:11]([Cl:12])=[CH:10][N:9]=[C:8]([NH:13][C:14]2[CH:15]=[C:16]([CH2:20][CH2:21][CH2:22]O)[CH:17]=[CH:18][CH:19]=2)[N:7]=1.B(Br)(Br)[Br:31].C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl.C(=O)=O>[Br:1][C:2]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][C:3]=1[CH2:4][NH:5][C:6]1[C:11]([Cl:12])=[CH:10][N:9]=[C:8]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][CH2:21][CH2:22][Br:31])[CH:15]=2)[N:7]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 25134Boron tribromideHCID 584678783-[3-({4-[(2-Bromo-5-methoxybenzyl)amino]-5-chloropyrimidin-2-yl)amino]phenyl}propan-1-ol

Product 1

HCID 584679264-Bromo-3-{[(2-{[3-(3-bromopropyl)phenyl]amino}-5-chloropyrimidin-4-yl)amino]methyl}phenolYield 91%

Reagents, catalysts & solvents 2

HCID 280Carbon DioxideSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-[3-({4-[(2-bromo-5-methoxybenzyl)amino]-5-chloropyrimidin-2-yl}amino)phenyl]propan-1-ol (3.0 g, 6.3 mmol) in methylene chloride (40 mL) was added slowly a solution of boron tribromide in methylene chloride (31 mL, 31 mmol, 1.0 M) at 0° C. The mixture was allowed to warm up to rt and stirred over the weekend. The resultant mixture was cooled in dry ice when Na2CO3 (saturated aqueous solution) was added. The mixture was filtered and the solid collected was triturated with EtOAc, followed by washing with cold water to give the desired product (3.0 grams, 91%) as an off-white powder. LCMS for C20H19Br2ClN4O (M+H)+: m/z=524.8, 526.8, 528.7.

Workup

  1. additionwas added
  2. filtrationThe mixture was filtered
  3. customthe solid collected
  4. customwas triturated with EtOAc
  5. washby washing with cold water

Sources & evidence

ORD record
ord-23e6ee683fec44ed87357cb874b0ce48
Source dataset
uspto-grants-2014_07
Patent number
US08765727B2

Reaction notes

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