3-Nitrophenol → HCID 88910519, compound

HRID 2359359Notes

Reaction equation

HRID 2359359 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH:10]=[CH:9][N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:6]=2[N:7]=1.[N+:20]([C:23]1[CH:24]=[C:25]([OH:29])[CH:26]=[CH:27][CH:28]=1)([O-:22])=[O:21].C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[N:3]=[C:4]([O:29][C:25]2[CH:26]=[CH:27][CH:28]=[C:23]([N+:20]([O-:22])=[O:21])[CH:24]=2)[C:5]2[CH:10]=[CH:9][N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 111373-NitrophenolHCID 11430Potassium CarbonateHCID 219764212,4-Dichloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 88910519HCID 88910519, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of Compound 6-B (200 mg, 0.628 mmol) and 3-nitrophenol (96.2 g, 0.691 mmol) in dimethylformamide (2 mL) was added K2CO3 (173.7 mg, 1.26 mmol). The reaction mixture was stirred at room temperature for 4 hours. The reaction mixture was then filtered. The filtrate was diluted with water, then extracted with ethyl acetate. The organic layer was washed with water, brine, and dried over Na2SO4. After filtration and removal of the volatiles in vacuo, the crude product was purified by flash column chromatography (PE/EA=20/1) affording Compound 6-C (200 mg, yield 75.6%, M+H+=421.92) as a white solid.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. additionThe filtrate was diluted with water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried over Na2SO4
  6. filtrationAfter filtration and removal of the volatiles in vacuo
  7. customthe crude product was purified by flash column chromatography (PE/EA=20/1)

Sources & evidence

ORD record
ord-cedef2b4bd864e37b96786ecd0c1dde5
Source dataset
uspto-grants-2014_04
Patent number
US08685988B2

Reaction notes

Loading…