Pyridine → HCID 58446806, compound

HRID 1958343Notes

Reaction equation

HRID 1958343 reaction equation
Br.[NH2:2][C:3]1[CH:8]=[CH:7][N:6]2[CH:9]=[C:10]([C:12]3[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=3)[N:11]=[C:5]2[N:4]=1.[C:19](OC(=O)C)(=[O:21])[CH3:20].N1C=CC=CC=1.C([O-])(O)=O.[Na+]>O>[NH2:2][C:3]1[CH:8]=[CH:7][N:6]2[CH:9]=[C:10]([C:12]3[CH:13]=[C:14]([O:18][C:19](=[O:21])[CH3:20])[CH:15]=[CH:16][CH:17]=3)[N:11]=[C:5]2[N:4]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 673879503-(7-Aminoimidazo[1,2-a]pyrimidin-2-yl)phenol hydrobromide

Product 1

HCID 58446806HCID 58446806, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

To a microwave vial were added 3-(7-aminoimidazo[1,2-a]pyrimidin-2-yl)phenol hydrobromide (500 mg, 1.63 mmol), acetic anhydride (199 mg, 185 μA, 1.95 mmol) and pyridine (5.00 ml). The vial was capped and heated in the microwave at 120° C. for 15 min. H2O was added to the reaction mixture and the pH was installed around 7-8 by addition of 10% NaHCO3 aq. solution. The product was extracted with CH2Cl2, then the solvent was partially evaporated and the formed solid was collected and purified by flash chromatography (SiO2 cartridge; eluent: CH2Cl2/MeOH/NH3aq. 140:10:1). White solid (207 mg, 45%).

Workup

  1. customThe vial was capped
  2. extractionThe product was extracted with CH2Cl2
  3. customthe solvent was partially evaporated
  4. customthe formed solid was collected
  5. custompurified by flash chromatography (SiO2 cartridge; eluent: CH2Cl2/MeOH/NH3aq. 140:10:1)

Sources & evidence

ORD record
ord-23c58876ba114e87b7ab7047b3753644
Source dataset
uspto-grants-2013_04
Patent number
US08410117B2

Reaction notes

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