Dimethylformamide → HCID 69860012, compound

HRID 394076Notes

Reaction equation

HRID 394076 reaction equation
C(=O)([O-])[O-].[K+].[K+].CN(C=O)C.[Br:12][C:13]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[C:15](Br)[C:14]=1[CH2:22][N:23](CC1C=CC(OC)=CC=1)[C:24]([NH:26]C1C(Cl)=CC=CC=1Cl)=[O:25].[NH4+].[OH-]>[Cu](I)I.O>[Br:12][C:13]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[C:15]2[C:14]=1[CH2:22][NH:23][C:24](=[O:25])[NH:26]2

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 14923Ammonium HydroxideHCID 22648071HCID 22648071, compound2×

Product 1

HCID 69860012HCID 69860012, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 962WaterSolvent

Procedure

To a flask containing dry, finely ground potassium carbonate (22.17 g, 0.160 mol) under a nitrogen atmosphere was added anhydrous DMF (800 ml), N-[(2,6-dibromo-4-methoxyphenyl)methyl]-N′-(2,6 dichlorophenyl)-N-[(4-methoxyphenyl)methyl]urea (32.25 g, 0.0535 mol) (INTERMEDIATE 21) and copper iodide (6.80 g, 0.0353 mol). After refluxing one hour the solution was cooled to RT and poured into a solution containing 700 mL NH4OH (28%) and water (8 L). The precipitated product was filtered, washed with water (5×500 mL), hexanes (4×500 mL) and air dried to give 1-(2,6-dichlorophenyl)-3-(4-methoxyphenyl)methyl]-5-bromo-7-methoxy-3,4-dihydro-2(1H)-quinazolinone. 1H NMR(CDCl3, 500 MHz): δ 3.67 (s, 3H), 3.83 (s, 3H), 4.44 (s, 2H), 4.68 (s, 2H), 5.59 (d, 1H, J=2.3 Hz), 674 (d, 1H, J=2.3 Hz), 6.91 (d, 2H, J=8.7 Hz), 7.34-7.37 (m, 3H), 7.50 (d, 2H, J=8.0 Hz), MS(ES) 521 (M+1); LC 1:4.15 min.

Workup

  1. additionTo a flask containing
  2. customdry
  3. temperatureAfter refluxing one hour the solution
  4. additionpoured into a solution
  5. filtrationThe precipitated product was filtered
  6. washwashed with water (5×500 mL), hexanes (4×500 mL) and air
  7. customdried

Sources & evidence

ORD record
ord-fd413f771dc44c068997375cd4697e80
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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