Potassium Carbonate → HCID 9977489, compound

HRID 1179258Notes

Reaction equation

HRID 1179258 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[C:11]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:10]=[C:9]([C:20]#[N:21])[N:8]=2)[N:5]=[C:4]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:3]=1.C([O-])([O-])=[O:30].[K+].[K+]>CS(C)=O.OO>[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[C:11]([NH:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:10]=[C:9]([C:20]([NH2:21])=[O:30])[N:8]=2)[N:5]=[C:4]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:3]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 58976508HCID 58976508, compound

Product 1

HCID 9977489HCID 9977489, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 784Hydrogen PeroxideCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

To (20 mg; 0.054 mMol) of 4-(5-amino-3-phenylamino-[1,2,4]triazol-1-yl)-6-phenylamino-pyrimidine-2-carbonitrile in 500 μL of DMSO was added, at ambient temperature, (5 mg; 0.036 mMol) of anhydrous K2CO3, followed by 10 drops of 30% aqueous H2O2. The reaction was stirred for 10 min and quenched with water. The aqueous layer was extracted with EtOAc (2×). The organic fractions were combined and washed with water, brine, and then dried (Na2SO4), filtered and concentrated. The solid was triturated with hot 2-propanol, allowed to cool and the solid was collected via suction filtration, washed with 2-propanol, and MTBE, and air-dried to provide an off white powder (61% yield).

Workup

  1. customquenched with water
  2. extractionThe aqueous layer was extracted with EtOAc (2×)
  3. washwashed with water, brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe solid was triturated with hot 2-propanol
  8. temperatureto cool
  9. filtrationthe solid was collected via suction filtration
  10. washwashed with 2-propanol, and MTBE
  11. customair-dried

Sources & evidence

ORD record
ord-fbe3b247a4ee4c3190e2bc1775a659c6
Source dataset
uspto-grants-2007_10
Patent number
US07279469B2

Reaction notes

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