Sodium Hydroxide → HCID 74818738, compound

HRID 28643Notes

Reaction equation

HRID 28643 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15](=O)[CH3:16])=[CH:11][CH:10]=2)[CH:5]=[C:4]([C:18]2[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=2[Cl:25])[N:3]=1.Cl.[NH2:27][OH:28].[OH-].[Na+]>C(O)C>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15](=[N:27][OH:28])[CH3:16])=[CH:11][CH:10]=2)[CH:5]=[C:4]([C:18]2[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=2[Cl:25])[N:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 68983732HCID 68983732, compound

Product 1

HCID 74818738HCID 74818738, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-{4-[2-amino-6-(2,5-dichloro-phenyl)-pyrimidin-4-yl-amino]-phenyl}-ethanone, hydroxylamine hydrochloride, 0.6 M aqueous sodium hydroxide solution (2 ml), and ethanol (20 ml) was stirred 16 hours. The mixture was extracted with tetrahydrofuran (3×15 ml). The combined extracts were dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on alumina eluting with 7% methanol-chloroform to provide the title compound (0.010 g, 10% yield). 1H NMR (DMSO-d6) δ 2.14 (s, 3H, CH3), 6.34 (s, 1H, Ar), 7.51-0.754 (m, 1H, Ar), 7.58-7.61 (m, 3H, Ar), 7.65 (d, 1H, J=2.5 Hz, Ar), 7.79 (d, 2H, J=8.8 Hz, Ar), 9.46 (s, 1H, NH), 11.02 (s, 1H, OH).

Workup

  1. extractionThe mixture was extracted with tetrahydrofuran (3×15 ml)
  2. dry with materialThe combined extracts were dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography on alumina eluting with 7% methanol-chloroform

Sources & evidence

ORD record
ord-18592666402b4945b8895f13d813cc88
Source dataset
uspto-grants-2008_09
Patent number
US07419984B2

Reaction notes

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