Water → HCID 136333902, compound

HRID 2407172Notes

Reaction equation

HRID 2407172 reaction equation
[NH2:1][C:2]1[N:3]=[N:4][C:5]([C:14]2[CH:15]=[CH:16][C:17]([O:24]C)=[C:18]([NH:20][C:21](=[O:23])[CH3:22])[CH:19]=2)=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1.COC.O>C(Cl)Cl>[NH2:1][C:2]1[N:3]=[N:4][C:5]([C:14]2[CH:15]=[CH:16][C:17]([OH:24])=[C:18]([NH:20][C:21](=[O:23])[CH3:22])[CH:19]=2)=[C:6]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8254Dimethyl EtherHCID 67365676HCID 67365676, compound

Product 1

HCID 136333902HCID 136333902, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

N-[5-(3-amino-5-phenyl-1,2,4-triazin-6-yl)-2-hydroxyphenyl]acetamide was prepared by O-demethylation of N-[5-(3-amino-5-phenyl-1,2,4-triazin-6-yl)-2-methoxyphenyl]acetamide (0.05 g, 0.15 mmol; vide supra). The methyl ether was dissolved in DCM (5 mL), cooled to −78° C. and treated with borontribromide (5.25 mmol, 1.32 g). The resulting mixture was gradually warmed to RT then stirred at this temperature for a further 16 hours. The mixture was poured into water (15 mL) and extracted with DCM (3×15 mL). The combined organic extracts were dried over Na2SO4, concentrated in vacuum and purified by gradient flash chromatography, eluting with 30% ethyl acetate in hexane to afford the target compound (0.30 g, 85%).

Workup

  1. additiontreated with borontribromide (5.25 mmol, 1.32 g)
  2. temperatureThe resulting mixture was gradually warmed to RT
  3. extractionextracted with DCM (3×15 mL)
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. concentrationconcentrated in vacuum
  6. custompurified by gradient flash chromatography
  7. washeluting with 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-e5fdddc88da249758067642a8e97a8a5
Source dataset
uspto-grants-2014_08
Patent number
US08809525B2

Reaction notes

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