Potassium Iodide → HCID 67254301, compound

HRID 1970248Notes

Reaction equation

HRID 1970248 reaction equation
[NH2:1][C:2]1[O:3][CH2:4][C@@:5]2([N:26]=1)[C:18]1[CH:17]=[C:16]([OH:19])[CH:15]=[CH:14][C:13]=1[O:12][C:11]1[C:6]2=[CH:7][C:8]([C:20]2[CH:21]=[N:22][CH:23]=[N:24][CH:25]=2)=[CH:9][CH:10]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+].CN(C=O)C.Cl[CH2:41][C:42](=[O:44])[CH3:43]>>[NH2:1][C:2]1[O:3][CH2:4][C@:5]2([N:26]=1)[C:6]1[CH:7]=[C:8]([C:20]3[CH:21]=[N:22][CH:23]=[N:24][CH:25]=3)[CH:9]=[CH:10][C:11]=1[O:12][C:13]1[C:18]2=[CH:17][C:16]([O:19][CH2:41][C:42](=[O:44])[CH3:43])=[CH:15][CH:14]=1

Participants

6

Reactant 5

HCID 4875Potassium IodideHCID 6228DimethylformamideHCID 6571ChloroacetoneHCID 10796Cesium carbonateHCID 59272383HCID 59272383, compound

Product 1

HCID 67254301HCID 67254301, compound

Procedure

A vial was charged with (S)-2-amino-7′-(pyrimidin-5-yl)-5H-spiro[oxazole-4,9′-xanthen]-2′-ol (192.0 mg, 554 μmol), cesium carbonate (271 mg, 832 μmol), and potassium iodide (92.0 mg, 554 μmol). DMF (2217 μl, 554 μmol) was added, the vial was sonicated for about 30 seconds, and the mixture was stirred vigorously for 20 min, at which time some white solid still remained. The vial was cooled in an ice-bath for 10 min, and to it chloroacetone (48.6 μl, 610 μmol) was added dropwise. The cooling bath was removed after 5 h, and the mixture was stirred for an additional 10 h. The reaction mixture was partitioned between water and EtOAc. The layers were separated and the aqueous layer was extracted with EtOAc (2×). The combined organic extracts were dried over sodium sulfate, filtered, and evaporated. The residue was purified by chromatography on a 40-g Redi-Sep column, eluting with 2.5%-10% MeOH/DCM to afford (S)-1-(2-amino-2′-(pyrimidin-5-yl)-5H-spiro[oxazole-4,9′-xanthene]-7′-yloxy)propan-2-one as a white solid. MS m/z=403.2 [M+H]+. Calc'd for C22H19N4O4: 403.1.

Workup

  1. customthe vial was sonicated for about 30 seconds
  2. temperatureThe vial was cooled in an ice-bath for 10 min
  3. customThe cooling bath was removed after 5 h
  4. stirringthe mixture was stirred for an additional 10 h
  5. customThe reaction mixture was partitioned between water and EtOAc
  6. customThe layers were separated
  7. extractionthe aqueous layer was extracted with EtOAc (2×)
  8. dry with materialThe combined organic extracts were dried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue was purified by chromatography on a 40-g Redi-Sep column
  12. washeluting with 2.5%-10% MeOH/DCM

Sources & evidence

ORD record
ord-18575bd22e7346e1ac3783c4ee244501
Source dataset
uspto-grants-2013_04
Patent number
US08426447B2

Reaction notes

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