Triethylamine → (R)-1-(4-(2-chloro-7-methylquinazolin-4-yl)piperazin-1-yl)-2-hydroxy-4-methylpentan-1-one

HRID 2062200Notes

Reaction equation

HRID 2062200 reaction equation
[Cl:1][C:2]1[N:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][C:6]([CH3:13])=[CH:7][CH:8]=2)[N:3]=1.C(N(CC)CC)C.[OH:21][C@H:22]([CH2:31][CH:32]([CH3:34])[CH3:33])[C:23]([N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)=[O:24]>C(Cl)Cl>[Cl:1][C:2]1[N:11]=[C:10]([N:28]2[CH2:27][CH2:26][N:25]([C:23](=[O:24])[C@H:22]([OH:21])[CH2:31][CH:32]([CH3:33])[CH3:34])[CH2:30][CH2:29]2)[C:9]2[C:4](=[CH:5][C:6]([CH3:13])=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 219419832,4-Dichloro-7-methylquinazolineHCID 59216548(R)-2-hydroxy-4-methyl-1-(piperazin-1-yl)pentan-1-one

Product 1

HCID 58010811(R)-1-(4-(2-chloro-7-methylquinazolin-4-yl)piperazin-1-yl)-2-hydroxy-4-methylpentan-1-oneYield 183%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,4-dichloro-7-methylquinazoline (2.09 g, 9.83 mmol) in CH2Cl2 (10 mL) at 0° C. was added triethylamine (2.74 mL, 19.66 mmol), followed by the addition of (R)-2-hydroxy-4-methyl-1-(piperazin-1-yl)pentan-1-one (1.97 g, 9.83 mmol). The reaction mixture was warmed to room temperature and stirred overnight. The mixture was then quenched with water and extracted twice with CH2Cl2. The combined organic extracts were dried over MgSO4, filtered, and concentrated to obtain (R)-1-(4-(2-chloro-7-methylquinazolin-4-yl)piperazin-1-yl)-2-hydroxy-4-methylpentan-1-one (6.78 g, 95%). LC/MS: m/z 377.5 (M+H)+ at 2.61 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customThe mixture was then quenched with water
  2. extractionextracted twice with CH2Cl2
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-501f8a4ca2e94ba89aee48925c8f0354
Source dataset
uspto-grants-2012_10
Patent number
US08283354B2

Reaction notes

Loading…