8-Chloro-10-(trifluoromethyl)pyrimido[5,4-b]quinolin-4(3H)-one → 10-(4-Bromobenzyl)-8-chloro-10-(trifluoromethyl)-5,10-dihydropyrimido[5,4-b]quinolin-4(3H)-one

HRID 456983Notes

Reaction equation

HRID 456983 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[C:7]3[C:12](=[O:16])[NH:13][CH:14]=[N:15][C:6]3=[C:5]([C:17]([F:20])([F:19])[F:18])[C:4]=2[CH:3]=1.[Br:21][C:22]1[CH:30]=[CH:29][C:25]([CH2:26][Mg]Br)=[CH:24][CH:23]=1>C1COCC1>[Br:21][C:22]1[CH:30]=[CH:29][C:25]([CH2:26][C:5]2([C:17]([F:18])([F:20])[F:19])[C:4]3[CH:3]=[C:2]([Cl:1])[CH:11]=[CH:10][C:9]=3[NH:8][C:7]3[C:12](=[O:16])[NH:13][CH:14]=[N:15][C:6]2=3)=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 1358136228-Chloro-10-(trifluoromethyl)pyrimido[5,4-b]quinolin-4(3H)-oneHCID 178419660HCID 178419660, compound

Product 1

HCID 13552236010-(4-Bromobenzyl)-8-chloro-10-(trifluoromethyl)-5,10-dihydropyrimido[5,4-b]quinolin-4(3H)-oneYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of 7 (200 mg, 0.667 mmol) in THF (4 mL) at −40° C. was added 4-bromobenzyl magnesium bromide (0.25 M in Et2O, 13.3 mL, 3.34 mmol). The reaction was warmed slowly to 0° C. over 2 h. After stirring an additional 2 h, the reaction was quenched with H2O (20 mL) and extracted with EtOAc (2×20 mL). The combined organic layers were washed with brine, dried (MgSO4) and concentrated. Chromatography (SiO2, 40 to 50% EtOAc-hexane) afforded the desired product as a viscous orange oil (134 mg, 43%). ESI-MS m/z 470.2 (M++H, C19H12BrClF3N3O).

Workup

  1. customthe reaction was quenched with H2O (20 mL)
  2. extractionextracted with EtOAc (2×20 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3bcaf7ae74f149e2844421215e92ed85
Source dataset
uspto-grants-2007_03
Patent number
US07186830B2

Reaction notes

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