Diisopropylamine → HCID 86757341, compound

HRID 1594838Notes

Reaction equation

HRID 1594838 reaction equation
[CH3:1][C:2]1([CH3:10])[CH:6]([C:7]#[CH:8])[O:5][C:4](=[O:9])[NH:3]1.[Cl:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19](I)[CH:20]=2)[N:15]=[CH:14][N:13]=1.C(NC(C)C)(C)C>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu](I)I>[Cl:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=[C:14]([C:8]#[C:7][CH:6]2[O:5][C:4](=[O:9])[NH:3][C:2]2([CH3:10])[CH3:1])[N:13]=1

Participants

7

Reactant 3

HCID 7912DiisopropylamineHCID 111738094-Chloro-6-iodoquinazolineHCID 18616463HCID 18616463, compound

Product 1

HCID 86757341HCID 86757341, compoundYield 72.2%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4,4-Dimethyl-5-ethynyl-2-oxazolidinone (1.10 g, 7.90 mmol), 4chloro-6-iodoquinazoline (1.63 g, 5.60 mmol), dichlorobis(triphenylphosphine)palladium(II) (200 mg, 0.28 mmol), copper iodide (53 mg, 0.28 mmol), and diisopropylamine (0.57 g, 5.60 mmol) in anhydrous THF (30 mL) was stirred at room temperature under nitrogen for 4 hours. After concentration, the residue was dissolved in CH2Cl2 (80 mL), washed with aqueous NH4Cl and brine, dried over sodium sulfate, and concentrated to give the crude product as brown oil. Purification by silica gel column using 50-70% EtOAc in hexane afforded 1.22 g (72%) of yellow solid: 1H NMR (CDCl3) δ 1.49 (s, 3H), 1.53 (s, 3H), 5.14 (s, 1H), 5.57 (brs, 1H), 7.95 (dd, 1H), 8.04 (d, 1H, J=8.8 Hz), 8.38 (d, 1H, J=2.0 Hz), 9.05 (s, 1H).

Workup

  1. concentrationAfter concentration
  2. dissolutionthe residue was dissolved in CH2Cl2 (80 mL)
  3. washwashed with aqueous NH4Cl and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customto give the crude product as brown oil
  7. customPurification by silica gel column

Sources & evidence

ORD record
ord-28412b27e04e430c9c67f029aaacb203
Source dataset
uspto-grants-2001_09
Patent number
US06284764B1

Reaction notes

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