Boron tribromide → HCID 136175016, compound

HRID 1027490Notes

Reaction equation

HRID 1027490 reaction equation
B(Br)(Br)Br.[Cl:5][C:6]1[CH:35]=[CH:34][C:9]([CH2:10][C:11]2[N:12]=[C:13]([O:30][CH2:31][CH2:32][CH3:33])[C:14]3[N:19]=[C:18]([C:20]4[CH:25]=[C:24]([CH3:26])[C:23]([O:27]C)=[C:22]([CH3:29])[CH:21]=4)[O:17][C:15]=3[N:16]=2)=[CH:8][CH:7]=1.C(=O)([O-])O.[Na+]>ClCCl>[Cl:5][C:6]1[CH:35]=[CH:34][C:9]([CH2:10][C:11]2[N:12]=[C:13]([O:30][CH2:31][CH2:32][CH3:33])[C:14]3[N:19]=[C:18]([C:20]4[CH:21]=[C:22]([CH3:29])[C:23]([OH:27])=[C:24]([CH3:26])[CH:25]=4)[O:17][C:15]=3[N:16]=2)=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 67177294HCID 67177294, compound

Product 1

HCID 136175016HCID 136175016, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

20 ml of a 1 M solution of boron tribromide in dichloromethane was added to 435 mg of 5-(4-chloro-benzyl)-2-(4-methoxy-3,5-dimethyl-phenyl)-7-propoxy-oxazolo[5,4-d]pyrimidine (example 168, prepared analogously to the preparation of the compound of example 5). The reaction mixture was stirred at room temperature for 30 min. Upon completion of the reaction the solution was cooled with ice and a saturated sodium hydrogencarbonate solution was added until the pH was adjusted to 7. Filtration of the precipitate yielded the crude product which was purified by preparative HPLC (method HPLC2) to give 263 mg of the title compound.

Workup

  1. customUpon completion of the reaction the solution
  2. temperaturewas cooled with ice
  3. filtrationFiltration of the precipitate
  4. customyielded the crude product which
  5. customwas purified by preparative HPLC (method HPLC2)

Sources & evidence

ORD record
ord-9a80e6eb195243e2944400890ccd4979
Source dataset
uspto-grants-2014_05
Patent number
US08735387B2

Reaction notes

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