Sodium Carbonate → HCID 58467888, compound

HRID 1614965Notes

Reaction equation

HRID 1614965 reaction equation
[Cl:1][C:2]1[C:3]([NH:18][CH2:19][CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([O:28]C)[CH:23]=2)=[N:4][C:5]([NH:8][C:9]2[CH:10]=[C:11]([CH2:15][CH2:16]O)[CH:12]=[CH:13][CH:14]=2)=[N:6][CH:7]=1.B(Br)(Br)[Br:31].C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl.C(=O)=O>[Br:31][CH2:16][CH2:15][C:11]1[CH:10]=[C:9]([NH:8][C:5]2[N:4]=[C:3]([NH:18][CH2:19][CH2:20][CH2:21][C:22]3[CH:23]=[C:24]([OH:28])[CH:25]=[CH:26][CH:27]=3)[C:2]([Cl:1])=[CH:7][N:6]=2)[CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 25134Boron tribromideHCID 584678952-{3-[(5-Chloro-4-{[3-(3-methoxyphenyl)propyl]amino}pyrimidin-2-yl)amino]phenyl}ethanol

Product 1

HCID 58467888HCID 58467888, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 280Carbon DioxideSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-{3-[(5-chloro-4-{[3-(3-methoxyphenyl)propyl]amino}pyrimidin-2-yl)amino]phenyl}ethanol (0.35 g, 0.73 mmol) in methylene chloride (4.7 mL) was added slowly a solution of boron tribromide in methylene chloride (3.6 mL, 3.6 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 Na2CO3 (saturated aqueous solution) was added. The mixture was filtered and the solid collected was triturated with EtOAc, followed by washing with EtOAc and water successively to give the desired product as an off-white powder (303 mg, 90%). LCMS for C21H23BrClN4O (M+H)+: m/z=461.0, 463.0. 1H NMR (400 MHz, CD3OD): δ 7.95 (s, 1H), 7.91 (s, 1H), 7.44 (d, J=7.2 Hz, 1H), 7.38 (m, 1H), 7.08 (m, 1H), 6.97 (s, 1H), 6.68 (d, J=2.8 Hz, 1H), 6.59 (m, 2H), 3.60 (m, 4H), 3.18 (m, 2H), 2.66 (t, J=7.6 Hz, 2H), 1.99 (t, J=7.6 Hz, 2H).

Workup

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

Sources & evidence

ORD record
ord-b805b24eff6c49728df032fd31bad3a5
Source dataset
uspto-grants-2014_07
Patent number
US08765727B2

Reaction notes

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