1,2-Dimethoxyethane → HCID 86711288, compound

HRID 336153Notes

Reaction equation

HRID 336153 reaction equation
[NH2:1][C:2]1[C:3]2[C:10](I)=[CH:9][N:8]([CH2:12][CH2:13][C@@H:14]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH:15]=[CH2:16])[C:4]=2[N:5]=[CH:6][N:7]=1.C(=O)([O-])[O-].[Na+].[Na+].CO[CH2:33][CH2:34]OC.C(=O)(O)[O-].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C.O>[NH2:1][C:2]1[C:3]2[C:10]([C:3]3[CH:4]=[N:8][C:12]4[C:33]([CH:34]=3)=[CH:16][CH:15]=[CH:14][CH:13]=4)=[CH:9][N:8]([CH2:12][CH2:13][C@@H:14]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH:15]=[CH2:16])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 516892Sodium BicarbonateHCID 86711287HCID 86711287, compound

Product 1

HCID 86711288HCID 86711288, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of (R)-tert-butyl (5-(4-amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)pent-1-en-3-yl)carbamate (3.2 g) obtained in Step 5,3-quinolineboronic acid (1.37 g), sodium carbonate (843 mg), tetrakis(triphenylphosphine)palladium (250 mg), DME (32 ml) and water (32 ml) was stirred under a nitrogen atmosphere at 100° C. for 6 hours. After cooling the reaction mixture, a saturated aqueous sodium bicarbonate solution and ethyl acetate were added thereto. The resulting mixture was stirred at room temperature for 30 minutes. After filtering off the insoluble matter, the organic layer was separated and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate, ethyl acetate/methanol) to obtain the title compound as a light-orange solid (3.21 g).

Workup

  1. temperatureAfter cooling the reaction mixture
  2. stirringThe resulting mixture was stirred at room temperature for 30 minutes
  3. filtrationAfter filtering off the insoluble matter
  4. customthe organic layer was separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was then distilled off under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate, ethyl acetate/methanol)

Sources & evidence

ORD record
ord-36681b467aaa4fb49070bf94c72b8b35
Source dataset
uspto-grants-2014_11
Patent number
US08889666B2

Reaction notes

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