Furan → HCID 178441855, compound

HRID 1975665Notes

Reaction equation

HRID 1975665 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.C([Li])CCC.[CH2:11]([C:15]1[NH:16][C:17]2[C:22]([C:23](=[O:25])[N:24]=1)=[CH:21][C:20]([CH:26]=[O:27])=[CH:19][CH:18]=2)[CH2:12][CH2:13][CH3:14]>O1CCCC1>[CH2:11]([C:15]1[NH:16][C:17]2[C:22]([C:23](=[O:25])[N:24]=1)=[CH:21][C:20]([CH:26]([C:2]1[O:1][CH:5]=[CH:4][CH:3]=1)[OH:27])=[CH:19][CH:18]=2)[CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 8029FuranHCID 178418339ButyllithiumHCID 178441857HCID 178441857, compound

Product 1

HCID 178441855HCID 178441855, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 7.88 ml of furan in 80 ml of dry tetrahydrofuran is cooled at 0° C. and 47.8 ml of n-butyl lithium (2.5 M in hexanes) is added dropwise. Stirring is continued for 1 hour at 0° C. and the mixture allowed to warm to room temperature. The reaction mixture is cooled to -78° C. and 5.0 g of 2-butyl-1,4-dihydro-4-oxo-6-quinazolinecarboxaldehyde added rapidly. The reaction mixture is stirred for 1.5 hours at -78° C., quenched with 100 ml of saturated ammonium chloride, allowed to warm to room temperature and the volatiles removed in vacuo. The reaction mixture is diluted with 500 ml of ethyl acetate and washed with water, 2N citric acid, 1M sodium bicarbonate and brine. The organic layer is dried and evaporated to a residue which crystallizes from ethyl acetate to afford 3.75 g of the desired product, m.p. 183°-185° C. An additional 700 mg of the desired product is obtained from the filtrate as white crystals m.p. 183°-185° C. Fab Mass Spec 299 (M+H).

Workup

  1. temperatureThe reaction mixture is cooled to -78° C.
  2. stirringThe reaction mixture is stirred for 1.5 hours at -78° C.
  3. customquenched with 100 ml of saturated ammonium chloride
  4. temperatureto warm to room temperature
  5. customthe volatiles removed in vacuo
  6. additionThe reaction mixture is diluted with 500 ml of ethyl acetate
  7. washwashed with water, 2N citric acid, 1M sodium bicarbonate and brine
  8. customThe organic layer is dried
  9. customevaporated to a residue which
  10. customcrystallizes from ethyl acetate

Sources & evidence

ORD record
ord-14c78436a50d4de29aaf53947d42ae72
Source dataset
uspto-grants-1994_02
Patent number
US05288720

Reaction notes

Loading…