Triethylamine → N'-[1-(2,6-dichlorobenzoyl)-5-fluoro-2-oxo-1,2-dihydro-pyrimidin-4-yl]-N,N-dimethylformamidine

HRID 1260413Notes

Reaction equation

HRID 1260413 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(N(CC)CC)C.[Cl:21][C:22]1[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[C:23]=1[C:24](Cl)=[O:25]>ClCCl>[Cl:21][C:22]1[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[C:23]=1[C:24]([N:6]1[CH:7]=[C:2]([F:1])[C:3]([N:9]=[CH:10][N:11]([CH3:13])[CH3:12])=[N:4][C:5]1=[O:8])=[O:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 783922,6-Dichlorobenzoyl chlorideHCID 178484257HCID 178484257, compound

Product 1

HCID 58138281N'-[1-(2,6-dichlorobenzoyl)-5-fluoro-2-oxo-1,2-dihydro-pyrimidin-4-yl]-N,N-dimethylformamidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an 8 mL screw-cap vial were added dichloromethane (CH2Cl2; 4 mL), N′-(5-fluoro-2-hydroxy-pyrimidin-4-yl)-N,N-dimethylformamidine (100 mg, 0.54 mmol), and triethylamine (Et3N; 120 mg, 1.2 mmol). To this mixture was added 2,6-dichlorobenzoyl chloride (113 mg, 0.54 mmol), and the resulting mixture was shaken at room temperature for 24 h. After evaporation to dryness, the residue was taken up in N,N-dimethylformamide (DMF; 2 mL), filtered, and placed directly onto a reverse phase chromatography column. After elution, the title compound was isolated as a pale yellow solid (75 mg, 39%): mp 185-187° C.; 1H NMR (300 MHz, CDCl3) δ 8.80 (s, 1H), 8.20 (d, J=5.6 Hz, 1H), 7.31-7.20 (m, 3H), 3.23 (s, 3H), 3.21 (s, 3H); ESIMS m/z 357 ([M+H]+).

Workup

  1. customTo an 8 mL screw-cap vial
  2. customAfter evaporation to dryness
  3. filtrationfiltered
  4. washAfter elution

Sources & evidence

ORD record
ord-78bb3212838b4f139135dca4f7a74d98
Source dataset
uspto-grants-2013_06
Patent number
US08470839B2

Reaction notes

Loading…