Ethyl Acetate → HCID 131726952, compound

HRID 747180Notes

Reaction equation

HRID 747180 reaction equation
F[C:2]1[CH:7]=[C:6]([C:8]2[C:9]([C:15]3[O:16][CH:17]=[CH:18][CH:19]=3)=[N:10][C:11]([NH2:14])=[N:12][CH:13]=2)[CH:5]=[CH:4][N:3]=1.[C-]#[N:21].[Na+].[C:23]([O:26]CC)(=O)[CH3:24]>CS(C)=O>[NH2:14][C:11]1[N:10]=[C:9]([C:15]2[O:16][CH:17]=[CH:18][CH:19]=2)[C:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([CH2:24][C:23]([NH2:21])=[O:26])[CH:7]=2)=[CH:13][N:12]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 8929Sodium CyanideHCID 23020412HCID 23020412, compound

Product 1

HCID 131726952HCID 131726952, compoundYield 3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

A suspension of 5-(2-fluoro-4-pyridyl)-4-(2-furyl)-2-pyrimidinylamine (300 mg, 1.17 mmol) and sodium cyanide in dimethylsulfoxide (3 ml) was stirred at 150° C. for 46 hours. After cooling as it was, the reaction mixture was diluted with ethyl acetate and washed with an aqueous solution of saturated ammonium chloride twice. The resulting organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was subjected to silica gel plate (developing solvent; dichloromethane:methanol=10:1) and then washed with diethyl ether, to give the title compound (10 mg, 3%) as a colorless solid.

Workup

  1. temperatureAfter cooling as it
  2. washwashed with an aqueous solution of saturated ammonium chloride twice
  3. dry with materialThe resulting organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. washwashed with diethyl ether

Sources & evidence

ORD record
ord-a29a9bf0b8814bc5a5170b2abebeae2f
Source dataset
uspto-grants-2008_07
Patent number
US07396836B2

Reaction notes

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