Cesium carbonate → 1-(3,3-dimethylbutoxy)-8-(pyrimidin-5-yl)-10H-chromeno[3,2-c]pyridin-10-one

HRID 1970266Notes

Reaction equation

HRID 1970266 reaction equation
Cl[C:2]1[C:7]2[C:8](=[O:22])[C:9]3[CH:10]=[C:11]([C:16]4[CH:17]=[N:18][CH:19]=[N:20][CH:21]=4)[CH:12]=[CH:13][C:14]=3[O:15][C:6]=2[CH:5]=[CH:4][N:3]=1.[CH3:23][C:24]([CH3:29])([CH3:28])[CH2:25][CH2:26][OH:27].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH3:23][C:24]([CH3:29])([CH3:28])[CH2:25][CH2:26][O:27][C:2]1[C:7]2[C:8](=[O:22])[C:9]3[CH:10]=[C:11]([C:16]4[CH:17]=[N:18][CH:19]=[N:20][CH:21]=4)[CH:12]=[CH:13][C:14]=3[O:15][C:6]=2[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 122333,3-Dimethyl-1-butanolHCID 592723441-chloro-8-(pyrimidin-5-yl)-10H-chromeno[3,2-c]pyridin-10-one

Product 1

HCID 592723821-(3,3-dimethylbutoxy)-8-(pyrimidin-5-yl)-10H-chromeno[3,2-c]pyridin-10-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

A resealable tube was charged with 1-chloro-8-(pyrimidin-5-yl)-10H-chromeno[3,2-c]pyridin-10-one (0.320 g, 1.033 mmol), 3,3-dimethyl-1-butanol (0.260 mL, 2.066 mmol), cesium carbonate (0.842 g, 2.58 mmol), and acetonitrile (10.0 mL). The system was flushed with argon, the tube was sealed, and the mixture stirred at 100° C. for 5 h. The material was partitioned between dichloromethane and water. The aqueous phase was separated and extracted with dichloromethane. The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated to afford a brown solid. This solid was purified via column chromatography on silica gel (RediSep 120 g column, gradient elution with 50-100% ethyl acetate-hexane) to afford 1-(3,3-dimethylbutoxy)-8-(pyrimidin-5-yl)-10H-chromeno[3,2-c]pyridin-10-one as a white solid. MS m/z=376.2 [M+H]+. Calcd for C22H21N3O3: 375.4.

Workup

  1. customThe system was flushed with argon
  2. customthe tube was sealed
  3. customThe material was partitioned between dichloromethane and water
  4. customThe aqueous phase was separated
  5. extractionextracted with dichloromethane
  6. washThe combined organic phases were washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto afford a brown solid
  11. customThis solid was purified via column chromatography on silica gel (RediSep 120 g column, gradient elution with 50-100% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-e7168e2c315145dc9afc6ef687197eb4
Source dataset
uspto-grants-2013_04
Patent number
US08426447B2

Reaction notes

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