Nitrogen → 3-(4-(diethylamino)-3-fluorophenyl)-2,6-dimethylpyrimidin-4(3H)-one

HRID 56093Notes

Reaction equation

HRID 56093 reaction equation
[CH2:1]([N:3]([CH2:12][CH3:13])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][C:5]=1[F:11])[CH3:2].C[Al](C)C.N#N.[NH:20](/[C:24](/[CH3:30])=[CH:25]\[C:26](OC)=[O:27])[C:21]([CH3:23])=O>C(Cl)Cl>[CH2:12]([N:3]([CH2:1][CH3:2])[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:26](=[O:27])[CH:25]=[C:24]([CH3:30])[N:20]=[C:21]2[CH3:23])=[CH:6][C:5]=1[F:11])[CH3:13]

Participants

6

Reactant 4

HCID 947NitrogenHCID 57053602-Butenoic acid, 3-(acetylamino)-, methyl ester, (2Z)-HCID 16682925TrimethylaluminumHCID 33788586N1,N1-Diethyl-2-fluorobenzene-1,4-diamine

Product 1

HCID 729482053-(4-(diethylamino)-3-fluorophenyl)-2,6-dimethylpyrimidin-4(3H)-oneYield 67.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N1,N1-diethyl-2-fluorobenzene-1,4-diamine (1.50 g, 8.23 mmol) in anhydrous CH2Cl2 (60 mL) was added trimethylaluminium (33 mL, 33 mmol, 1 M in heptane) dropwise slowly under N2. Upon the end of addition the mixture was stirred at rt for 40 min. To this mixture was added a solution of methyl 3-acetaminocrotonate (2.58 g, 16.40 mmol) in anhydrous CH2Cl2 (20 mL). The resulting reaction mixture was stirred at rt for another 6 h, then quenched with water. The organic phase was washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo. The crude product was recrystallized from EtOAc to give the title compound as a pale yellow solid (1.60 g, 67%). The compound was characterized by the following spectroscopic data:

Workup

  1. additionUpon the end of addition the mixture
  2. customThe resulting reaction mixture
  3. stirringwas stirred at rt for another 6 h
  4. customquenched with water
  5. washThe organic phase was washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe crude product was recrystallized from EtOAc

Sources & evidence

ORD record
ord-94eabd851d1244438feb67797c89160b
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

Loading…