Ethenone, (trimethylsilyl)- → HCID 11360360, compound

HRID 1864483Notes

Reaction equation

HRID 1864483 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[N:14][C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([F:22])[CH:16]=1)/[N:9]=[CH:10]/N(C)C.C[Si]([CH:27]=[C:28]=[O:29])(C)C>C(OCC)(=O)C.C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:14]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([F:22])[CH:16]=2)[C:28](=[O:29])[CH:27]=[CH:10][N:9]=1

Participants

5

Reactant 2

HCID 77686Ethenone, (trimethylsilyl)-HCID 178426517HCID 178426517, compound

Product 1

HCID 11360360HCID 11360360, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
23 °C

Procedure

A solution of 2-bromo-N-[(1E)-(dimethylamino)methylidene]-N′-(3-fluoro-4-methylphenyl)benzenecarboximidamide (1-3, 500 mg, 1.38 mmol, 1.0 equiv) in ethyl acetate (5 mL) was treated with a solution of (trimethylsilyl)ketene (0.39 mL, 2.76 mmol, 2 equiv) in toluene (5 mL). The reaction mixture was stirred at 23° C. for 5 days. The resulting mixture was concentrated, and the residue was purified via reverse-phase HPLC (Acetonitrile:H2O gradient with 0.1% TFA present) to afford 2-(2-bromophenyl)-3-(3-fluoro-4-methylphenyl)pyrimidin-4(3H)-one (1-4) as a dark orange solid. 1H NMR (500 MHz, CD3OD) δ 8.12 (d, 1H, J=6.8 Hz), 7.53 (d, 1H, J=7.8 Hz), 7.46 (d, 1H, J=7.6 Hz), 7.32 (t, 1H, J=7.6 Hz), 7.24 (t, 1H, J=7.8 Hz), 7.20-7.08 (m, 3H), 6.67 (d, 1H, J=6.6 Hz), 2.19 (s, 3H).

Workup

  1. concentrationThe resulting mixture was concentrated
  2. customthe residue was purified via reverse-phase HPLC (Acetonitrile:H2O gradient with 0.1% TFA present)

Sources & evidence

ORD record
ord-526deb9b41824c50a49982d02eceb467
Source dataset
uspto-grants-2009_12
Patent number
US07625912B2

Reaction notes

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