Dimethylformamide → HCID 86679606, compound

HRID 577661Notes

Reaction equation

HRID 577661 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[C:10]([F:11])=[CH:9][N:8]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:6]=2[N:7]=1.[N+:21]([C:24]1[CH:25]=[C:26]([OH:30])[CH:27]=[CH:28][CH:29]=1)([O-:23])=[O:22].CN(C=O)C.C([O-])([O-])=O.[K+].[K+]>CCOC(C)=O.O>[Cl:1][C:2]1[N:3]=[C:4]([O:30][C:26]2[CH:27]=[CH:28][CH:29]=[C:24]([N+:21]([O-:23])=[O:22])[CH:25]=2)[C:5]2[C:10]([F:11])=[CH:9][N:8]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:6]=2[N:7]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 111373-NitrophenolHCID 11430Potassium CarbonateHCID 86679607HCID 86679607, compound

Product 1

HCID 86679606HCID 86679606, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a vial containing 2,4-dichloro-5-fluoro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine (389.5 mg, 1.2 mmol) was added m-nitrophenol (161 mg, 1.2 mmol), DMF (5 mL) and K2CO3 (320 mg, 2.3 mmol). The reaction mixture was heated at 60° C. for 1 hr. The reaction was diluted with EtOAc (120 mL) and water (30 mL). The organic layer was separated, washed with water (20 mL) and brine (20 mL), dried over Na2SO4 and evaporated to give an oil. The oil was purified via flash chromatography eluting with 100% heptanes. The solvent was removed to afford the title compound (505 mg, 99% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.34 (t, J=2.27 Hz, 1H) 8.22-8.28 (m, 1H) 7.90-7.96 (m, 1H) 7.86 (d, J=8.31 Hz, 1H) 7.78-7.84 (m, 1H) 5.59 (s, 2H) 3.54-3.66 (m, 2H) 0.84-0.99 (m, 2H) 0.00 (s, 9H). m/z (APCI+) for C18H20ClFN4O4Si 439.1 (M+H)+.

Workup

  1. customThe organic layer was separated
  2. washwashed with water (20 mL) and brine (20 mL)
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customto give an oil
  6. customThe oil was purified via flash chromatography
  7. washeluting with 100% heptanes
  8. customThe solvent was removed

Sources & evidence

ORD record
ord-6ee0c219ec4e46ed8e450057aff85d56
Source dataset
uspto-grants-2015_05
Patent number
US09040547B2

Reaction notes

Loading…