Dimethylformamide → HCID 58337740, compound

HRID 1887451Notes

Reaction equation

HRID 1887451 reaction equation
F[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([I:11])[CH:3]=1.[OH:12][C:13]1[CH:14]=[N:15][CH:16]=[N:17][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>Cl>[I:11][C:4]1[CH:3]=[C:2]([CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=1)[O:12][C:13]1[CH:14]=[N:15][CH:16]=[N:17][CH:18]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 2590861-Fluoro-3-iodo-5-nitrobenzeneHCID 565855Pyrimidin-5-ol

Product 1

HCID 58337740HCID 58337740, compoundYield 168.8%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
100 °C

Procedure

Two vials were each charged with 1-fluoro-3-iodo-5-nitrobenzene (1.0 g, 3.8 mmol, 1.0 eq), 5-hydroxypyrimidine (430 mg, 4.47 mmol, 1.20 eq), potassium carbonate (780 mg, 5.64 mmol, 1.50 eq), and DMF (12 mL) and stirred overnight at 100° C. The reaction mixtures were combined, diluted with 0.5N HCl, and extracted (3×) with CH2Cl2. The combined organics were dried (MgSO4), filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel afforded 2.2 g (87%) of the title compound as a yellow solid: 1H NMR (400 MHz, CDCl3) δ 9.13 (s, 1H), 8.58 (s, 2H), 8.38 (t, J=1.8 Hz, 1H), 7.82 (t, J=2.2 Hz, 1H), 7.70 (dd, J=2.3, 1.4 Hz, 1H); ES-MS [M+1]+: 344.0.

Workup

  1. customThe reaction mixtures
  2. extractionextracted (3×) with CH2Cl2
  3. dry with materialThe combined organics were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-144c48f937ba46339b3cdc09dd689ce6
Source dataset
uspto-grants-2013_08
Patent number
US08501757B2

Reaction notes

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