Diethyl Ether → HCID 178441842, compound

HRID 1974931Notes

Reaction equation

HRID 1974931 reaction equation
[CH2:1]([C:5]1[NH:6][C:7]2[C:12]([C:13](=[O:15])[N:14]=1)=[CH:11][C:10](C(OC)=O)=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH3:4].[CH3:20][Mg]Br.C([O:25][CH2:26][CH3:27])C>O1CCCC1.O>[CH2:1]([C:5]1[NH:6][C:7]2[C:12]([C:13](=[O:15])[N:14]=1)=[CH:11][C:10]([C:26]([OH:25])([CH3:27])[CH3:20])=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 178418573HCID 178418573, compoundHCID 178441861methyl 2-butyl-4-oxo-1H-quinazoline-6-carboxylate

Product 1

HCID 178441842HCID 178441842, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 0.075 g of methyl 2-butyl-1,4-dihydro-4-oxo-6-quinazolinecarboxylate in 5 ml of dry tetrahydrofuran, cooled to 0° C., is added dropwise 0.51 mol of a solution of 3.0M methylmagnesium bromide in diethyl ether. The reaction is stirred at 0° C. for 0.5 hours and then at room temperature for 1 hour followed by quenching with 10 ml of saturated ammonium chloride solution. The resulting reaction mixture is diluted with 10 ml of water and extracted with ethyl acetate. The combined organics are dried over magnesium sulfate, filtered and concentrated in vacuo. The residue is purified by flash chromatography on silica gel, eluting with 100:0.25 chloroform-methanol to yield 0.055 g of the desired product as a white solid, m.p. 190°-192° C.

Workup

  1. waitat room temperature for 1 hour followed
  2. customby quenching with 10 ml of saturated ammonium chloride solution
  3. customThe resulting reaction mixture
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined organics are dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by flash chromatography on silica gel
  9. washeluting with 100:0.25 chloroform-methanol

Sources & evidence

ORD record
ord-30d5373eef9445198b93aad9dbd3fcbb
Source dataset
uspto-grants-1994_02
Patent number
US05284852

Reaction notes

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