(2-Bromoethyl)cyclohexane → 3-(2-aminoquinazolin-6-yl)-1-(2-cyclohexylethyl)-4-methylpyridin-2(1H)-one

HRID 558464Notes

Reaction equation

HRID 558464 reaction equation
[NH2:1][C:2]1[N:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]3[C:13](=[O:19])[NH:14][CH:15]=[CH:16][C:17]=3[CH3:18])[CH:8]=2)[N:3]=1.CC(C)([O-])C.[Na+].Br[CH2:27][CH2:28][CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1>CN(C=O)C>[NH2:1][C:2]1[N:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]3[C:13](=[O:19])[N:14]([CH2:27][CH2:28][CH:29]4[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]4)[CH:15]=[CH:16][C:17]=3[CH3:18])[CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 15440(2-Bromoethyl)cyclohexaneHCID 23676156Sodium t-butoxideHCID 669999863-(2-aminoquinazolin-6-yl)-4-methylpyridin-2(1H)-one

Product 1

HCID 250687833-(2-aminoquinazolin-6-yl)-1-(2-cyclohexylethyl)-4-methylpyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(2-aminoquinazolin-6-yl)-4-methylpyridin-2(1H)-one (103 mg, 408 μmol, Example 1, step 3) in DMF in a sealed tube was added sodium tert-butoxide (58.9 mg, 612 μmol). The mixture was stirred at RT for 5 min and turned from clear yellow to a suspension of yellow solids. 1-bromo-2-cyclohexylethane (76.7 μl, 490 μmol) was then added and the resulting mixture was heated to 70° C. over the weekend. Reaction was cooled to RT and was quenched with Sat'd NH4Cl and extracted with DCM. Purification by prep plate TLC (10% MeOH/DCM) produced the title compound as an off white solid. M+H=363.2.

Workup

  1. additionclear yellow to a suspension of yellow solids
  2. temperaturethe resulting mixture was heated to 70° C. over the weekend
  3. customReaction
  4. temperaturewas cooled to RT
  5. customwas quenched with Sat'd NH4Cl
  6. extractionextracted with DCM
  7. customPurification by prep plate TLC (10% MeOH/DCM)

Sources & evidence

ORD record
ord-8feb50ed65f246b1a92701b93ee2d9bb
Source dataset
uspto-grants-2011_11
Patent number
US08063055B2

Reaction notes

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