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Boron tribromide → 4-[5-(2-Fluorophenoxy)oxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethylphenol

HRID 576912
Notes
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Reaction equation

HRID 576912 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[O:4][C:5]1[N:6]=[CH:7][C:8]2[N:13]=[C:12]([C:14]3[CH:19]=[C:18]([CH3:20])[C:17]([O:21]C)=[C:16]([CH3:23])[CH:15]=3)[O:11][C:9]=2[N:10]=1.B(Br)(Br)Br.C(=O)([O-])O.[Na+]>ClCCl>[F:1][C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[O:4][C:5]1[N:6]=[CH:7][C:8]2[N:13]=[C:12]([C:14]3[CH:15]=[C:16]([CH3:23])[C:17]([OH:21])=[C:18]([CH3:20])[CH:19]=3)[O:11][C:9]=2[N:10]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 25134Boron tribromide2×HCID 516892Sodium BicarbonateHCID 533113735-(2-Fluoro-phenoxy)-2-(4-methoxy-3,5-dimethyl-phenyl)-oxazolo[5,4-d]pyrimidine

Product 1

HCID 1361211154-[5-(2-Fluorophenoxy)oxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethylphenolYield 90.7%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
3×

Conditions

Temperature
0 °C

Procedure

A solution of 510 mg of 5-(2-fluoro-phenoxy)-2-(4-methoxy-3,5-dimethyl-phenyl)-oxazolo[5,4-d]pyrimidine in 20 ml of dichloromethane was cooled to 0° C. Over a period of 10 min, 4.2 ml of a 1 M solution of boron tribromide in dichloromethane was added. The mixture was stirred at 0° C. for 1 h, and then another 2 ml of a 1 M solution of boron tribromide in dichloromethane were added. After stirring for another 1 h, 10 ml of a saturated aqueous solution of sodium hydrogencarbonate were added slowly. The aqueous layer was extracted twice with 15 ml of dichloromethane, and the combined organic layers were dried over sodium sulfate, filtered. The solvents were removed in vacuo to give 445 mg of the title compound as a white solid. LC/MS (method LC2): Rt=3.62 min; m/z=352.13 [M+H]+

Workup

  1. stirringAfter stirring for another 1 h
  2. extractionThe aqueous layer was extracted twice with 15 ml of dichloromethane
  3. dry with materialthe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-fbcc6ef97e944388a553ebab3aaff62d
Source dataset
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09040544B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes