Potassium Carbonate → HCID 58166421, compound

HRID 1405971Notes

Reaction equation

HRID 1405971 reaction equation
[F:1][C:2]1[C:3]([N:9]=[CH:10][N:11]([CH3:13])[CH3:12])=[N:4][C:5]([OH:8])=[N:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[F:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Br)=[CH:23][CH:22]=1>CN(C)C=O>[F:1][C:2]1[C:3]([N:9]=[CH:10][N:11]([CH3:13])[CH3:12])=[N:4][C:5](=[O:8])[N:6]([CH2:25][C:24]2[CH:27]=[CH:28][C:21]([F:20])=[CH:22][CH:23]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 680214-Fluorobenzyl bromideHCID 178484257HCID 178484257, compound

Product 1

HCID 58166421HCID 58166421, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To an 8 mL screw-cap vial was added N,N-dimethylformamide (DMF; 1.5 mL), N′-(5-fluoro-2-hydroxypyrimidin-4-yl)-N,N-dimethylformamidine (100 mg, 0.54 mmol), anhydrous potassium carbonate (K2CO3; 138 mg, 1.0 mmol), and 4-fluorobenzyl bromide (113 mg, 0.60 mmol). The mixture was shaken and heated to 70° C. for 2 h and then at room temperature for an additional 16 h. The crude reaction mixture was filtered and placed directly onto a reverse phase chromatography column. After elution, the title compound was isolated as a white solid (30 mg, 20%): mp 134-136° C.; 1H NMR (300 MHz, CDCl3) δ 8.68 (s, 1H), 8.07 (d, J=2.5 Hz, 1H), 7.49-7.43 (m, 2H), 7.10-7.01 (m, 2H), 5.33 (s, 2H), 3.20 (s, 3H), 3.18 (s, 3H); ESIMS m/z 293 ([M+H]+).

Workup

  1. customTo an 8 mL screw-cap vial
  2. customThe crude reaction mixture
  3. filtrationwas filtered
  4. washAfter elution

Sources & evidence

ORD record
ord-c1a90bf9a1fc4a5e8c0f1aa452d0e059
Source dataset
uspto-grants-2014_12
Patent number
US08916579B2

Reaction notes

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