Ethanol → HCID 178436777, compound

HRID 1509049Notes

Reaction equation

HRID 1509049 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]2[N:12]=[C:11]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([CH2:20][C:21]#[N:22])=[CH:16][CH:15]=3)[C:10]([CH2:23][CH3:24])=[C:9]([CH3:25])[N:8]=2)=[CH:4][CH:3]=1.[NH2:26][OH:27].Cl.C([O-])([O-])=O.[K+].[K+].CCO>O>[Cl:1][C:2]1[S:6][C:5]([C:7]2[N:12]=[C:11]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([CH2:20][C:21]([NH:26][OH:27])=[NH:22])=[CH:16][CH:15]=3)[C:10]([CH2:23][CH3:24])=[C:9]([CH3:25])[N:8]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 90109864HCID 90109864, compound

Product 1

HCID 178436777HCID 178436777, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 50-mL round bottomed flask was charged with 2-[4-[[2-(5-Chloro-2-thienyl)-5-ethyl-6-methyl-pyrimidin-4-yl]amino]phenyl]acetonitrile (120 mg, 0.325 mmol, 1 eq.), NH2OH/HCl (160 mg, 2.3 mmol, 7 eq), K2CO3 (320 mg, 2.3 mol, 7 eq.), EtOH (10 ml) and water (1 ml). The mixture was stirred under reflux overnight. After cooling to room temperature, the volatile material was removed under reduced pressure. The residue was purified by chromatography on silica gel using 1.5˜4% of methanol in dichloromethane as eluent to give the title compound (61 mg, 47% yield).

Workup

  1. temperatureunder reflux overnight
  2. customthe volatile material was removed under reduced pressure
  3. customThe residue was purified by chromatography on silica gel using 1.5˜4% of methanol in dichloromethane as eluent

Sources & evidence

ORD record
ord-2c260272241844cbab0132d2a1c720c9
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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