Sodium hydride → HCID 45118278, compound

HRID 1250228Notes

Reaction equation

HRID 1250228 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[N:13]=[C:12]([CH3:15])[NH:11][C:10]2=[O:16].[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH:27]([CH2:30][CH2:31][CH2:32]I)[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]>CN(C=O)C.CCOC(C)=O>[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH:27]([CH2:30][CH2:31][CH2:32][N:11]2[C:10](=[O:16])[C:9]3[C:14](=[C:5]([O:4][CH3:3])[CH:6]=[CH:7][CH:8]=3)[N:13]=[C:12]2[CH3:15])[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 9975355Tert-butyl 4-(3-iodopropyl)piperidine-1-carboxylateHCID 1354111468-methoxy-2-methyl-3H-quinazolin-4-one

Product 1

HCID 45118278HCID 45118278, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Sodium hydride (91 mg, 2.37 mmol) was added to a solution of 8-methoxy-2-methyl-3H-quinazolin-4-one (300 mg, 1.58 mmol) in DMF (30 mL). The reaction mixture was stirred at 80° C. for 0.75 h and cooled to room temperature, then a solution of 4-(3-iodo-propyl)-piperidine-1-carboxylic acid tert-butyl ester (837 mg, 2.37 mmol) in DMF (1 mL) was added. The reaction mixture was heated at 85° C. for 17 h and diluted with EtOAc. The organic solution was washed with water and sat'd aq NaCl, dried and concentrated. Purification on SiO2-gel chromatography (50% EtOAc/hexanes) provided the desired product as a yellow oil. API-MS: 416 (M+1).

Workup

  1. temperaturecooled to room temperature
  2. temperatureThe reaction mixture was heated at 85° C. for 17 h
  3. washThe organic solution was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customPurification on SiO2-gel chromatography (50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-ea26a84cb6864aee9bafb18ce36bcedd
Source dataset
uspto-grants-2002_01
Patent number
US06337332B1

Reaction notes

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