Water → HCID 178481614, compound

HRID 538035Notes

Reaction equation

HRID 538035 reaction equation
C[O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][N:12]2[C:21](=[O:22])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][C:13]2=[O:23])[CH2:7][CH2:6]1)=[O:4].[H-].[Na+].[CH3:26]I.O>C1COCC1>[CH3:26][N:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:21](=[O:22])[N:12]([CH2:11][C@H:8]2[CH2:7][CH2:6][C@H:5]([C:3]([OH:2])=[O:4])[CH2:10][CH2:9]2)[C:13]1=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178501110HCID 178501110, compound

Product 1

HCID 178481614HCID 178481614, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

trans-4-(2,4-Dioxo-1,4-dihydro-2H-quinazolin-3-ylmethyl)-cyclohexane carboxylic acid methyl ester (1.5 g, 4.7 mmol) was dissolved in dry THF (20 ml) under nitrogen atmosphere. NaH (0.125 g, 5.2 mmol 60% in mineral oil) was added at 0° C. The reaction mixture was allowed to reach ambient temperature and then CH3I (324 μL, 5.2 mmol) was added. The reaction mixture was left stirring at room temperature for 24 hours, few drops of water were added and the solvent was removed under reduced pressure. The residue was suspended in water and 112 mg of NaOH were added. The mixture was heated at 100° C. for 30 minutes. The solution was allowed to reach room temperature and acidified to pH 3 with HCl 6N with the formation of a white precipitate which was isolated by filtration. (1.0 g, yield 66%)

Workup

  1. customto reach ambient temperature
  2. waitThe reaction mixture was left
  3. customthe solvent was removed under reduced pressure
  4. addition112 mg of NaOH were added
  5. temperatureThe mixture was heated at 100° C. for 30 minutes
  6. customto reach room temperature
  7. customwas isolated by filtration

Sources & evidence

ORD record
ord-fcbf22f81945446d8eeaa748dc806549
Source dataset
uspto-grants-2014_10
Patent number
US08865704B2

Reaction notes

Loading…