Dimethylformamide → HCID 46178256, compound

HRID 1970241Notes

Reaction equation

HRID 1970241 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][C:8]([C:16]4[CH:17]=[N:18][CH:19]=[N:20][CH:21]=4)=[CH:9][CH:10]=3)[C:5]3([CH2:25][O:24][C:23]([NH2:26])=[N:22]3)[C:4]=2[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C=O)C.Br[CH2:39][C:40]([CH3:43])([CH3:42])[CH3:41]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH3:39][C:40]([CH3:43])([CH3:42])[CH2:41][O:1][C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][C:8]([C:16]4[CH:17]=[N:18][CH:19]=[N:20][CH:21]=4)=[CH:9][CH:10]=3)[C:5]3([CH2:25][O:24][C:23]([NH2:26])=[N:22]3)[C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonate2×HCID 124151-Bromo-2,2-dimethylpropane2×HCID 584661412'-Hydroxy-7'-(5-pyrimidinyl)spiro[1,3-oxazole-4,9'-xanthen]-2-amine

Product 1

HCID 46178256HCID 46178256, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalyst2×HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A glass vial was charged with 2′-hydroxy-7′-(5-pyrimidinyl)spiro[1,3-oxazole-4,9′-xanthen]-2-amine (prepared as described in Example 3; 159 mg, 459 μmol), tetrabutylammonium iodide (84.8 mg, 230 μmol), cesium carbonate (374 mg, 1148 μmol), DMF (1.8 mL), and 1-bromo-2,2-dimethylpropane (175 μl, 1377 μmol). The vial was sealed and heated in a Biotage Initiator microwave reactor for 2 h at 100° C. Additional portions of tetrabutylammonium iodide (85 mg), cesium carbonate (180 mg), and 1-bromo-2,2-dimethylpropane (100 uL) were added. The vial was again heated in the microwave for 2 h at 100° C. The mixture was poured into water (10 mL) and extracted with EtOAc (3×10 mL). The combined organic extracts were dried over sodium sulfate, filtered, and evaporated. The residue was purified by chromatography on silica gel (eluting with 0-80% of a 90:10:1 DCM/MeOH/NH4OH mixture in DCM) to give 2′-(2,2-dimethylpropoxy)-7′-(5-pyrimidinyl)spiro[1,3-oxazole-4,9′-xanthen]-2-amine of a pale orange glass that solidified into an off-white solid. MS m/z=417.2 [M+H]+. Calc'd for C24H25N4O3: 417.2.

Workup

  1. customThe vial was sealed
  2. temperatureThe vial was again heated in the microwave for 2 h at 100° C
  3. extractionextracted with EtOAc (3×10 mL)
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by chromatography on silica gel (eluting with 0-80% of a 90:10:1 DCM/MeOH/NH4OH mixture in DCM)

Sources & evidence

ORD record
ord-e155c50362814c49807f8dbe935ae329
Source dataset
uspto-grants-2013_04
Patent number
US08426447B2

Reaction notes

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