Sodium hydride → HCID 59813341, compound

HRID 1925249Notes

Reaction equation

HRID 1925249 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]([C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([OH:17])[CH:13]=2)[CH:8]=1)=[O:6].Cl[C:19]1[C:28]2[C:23](=[CH:24][C:25]([O:31][CH3:32])=[C:26]([O:29][CH3:30])[CH:27]=2)[N:22]=[CH:21][N:20]=1>CN(C=O)C>[CH3:30][O:29][C:26]1[CH:27]=[C:28]2[C:23](=[CH:24][C:25]=1[O:31][CH3:32])[N:22]=[CH:21][N:20]=[C:19]2[O:17][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:5]([O:4][CH3:3])=[O:6])[CH:16]=[CH:15]2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 390995Methyl 6-hydroxy-2-naphthoateHCID 27693644-Chloro-6,7-dimethoxyquinazoline

Product 1

HCID 59813341HCID 59813341, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred mixture of NaH (200 mg, 60% in mineral oil, 5.0 mmol, Aldrich) in 10 mL of DMF at RT was added 6-hydroxy-naphthalene-2-carboxylic acid methyl ester (Step a, 675 mg, 3.34 mmol). After 20 min, 4-chloro-6,7-dimethoxy-quinazoline (750 mg, 3.34 mmol, Oakwood) was added and the reaction was heated to 60° C. for 20 min. The reaction was cooled to RT, quenched with saturated aqueous NH4Cl solution (30 mL) and extracted with CHCl3 (30 mL). The organic solution was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography (30% EtOAc/hexane) to give the title compound as a white solid. MS (ESI, pos. ion) m/z: 390.9 (M+1). Mass Calc'd for C22H18N2O5: 390.12.

Workup

  1. temperatureThe reaction was cooled to RT
  2. customquenched with saturated aqueous NH4Cl solution (30 mL)
  3. extractionextracted with CHCl3 (30 mL)
  4. washThe organic solution was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (30% EtOAc/hexane)

Sources & evidence

ORD record
ord-9cedcfb2407247b9ab0f04471fa47c1e
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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