Lithium Hydroxide → HCID 136248868, compound

HRID 922408Notes

Reaction equation

HRID 922408 reaction equation
Cl.F[C:3]1[CH:12]=[C:11]2[C:6]([C:7](=[O:28])[NH:8][C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([N:19]4[CH2:24][CH2:23][N:22]([CH:25](C)C)[CH2:21][CH2:20]4)[N:14]=3)=[N:10]2)=[C:5]([O:29][CH3:30])[CH:4]=1.[CH2:31]([O:38]C1C=CC(OC)=C(C=1)C=O)C1C=CC=CC=1.[OH-:49].[Li+]>C1OCCOCCOCCOCCOC1>[CH3:30][O:29][C:5]1[CH:4]=[C:3]([O:38][CH3:31])[CH:12]=[C:11]2[C:6]=1[C:7](=[O:28])[NH:8][C:9]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([N:19]3[CH2:20][CH2:21][N:22]([CH3:25])[C:23](=[O:49])[CH2:24]3)[N:14]=1)=[N:10]2

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 109666945-(Benzyloxy)-2-methoxybenzaldehydeHCID 136248856HCID 136248856, compound

Product 1

HCID 136248868HCID 136248868, compoundYield 18.2%

Reagents, catalysts & solvents 1

HCID 3633615-Crown-5Solvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-(6-bromopyridin-2-yl)-5,7-dimethoxyquinazolin-4(3H)-one (5 Scheme 21, 0.100 g, 0.278 mmol), 1-methylpiperazin-2-one (7, 0.100 g, 0.667 mmol) and anhydrous lithium hydroxide (0.020 g, 0.83 mmol) in 15-crown-5 (0.9 mL) was heated at 100° C. for 18 h. The mixture was cooled to room temperature and purified by reverse phase HPLC eluting with 10% to 90% CH3CN in H2O to afford the title compound (0.02 g, 18%) as an off-white solid: 1H NMR (500 MHz, DMSO-d6) δ 11.33 (s, 1H), 7.78 (t, J=7.5 Hz, 1H), 7.73 (d, J=7.1 Hz, 1H), 7.08 (d, J=8.3 Hz, 1H), 6.78 (d, J=2.2 Hz, 1H), 6.58 (d, J=2.2 Hz, 1H), 4.25 (s, 2H), 3.97 (t, J=5.5 Hz, 2H), 3.91 (s, 3H), 3.87 (s, 3H), 3.47 (t, J=5.3 Hz, 2H), 2.93 (s, 3H); ESI MS m/z 396 [M+H]+.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. custompurified by reverse phase HPLC
  3. washeluting with 10% to 90% CH3CN in H2O

Sources & evidence

ORD record
ord-57945974b7db4212b311dbb1d0ccb95b
Source dataset
uspto-grants-2016_03
Patent number
US09278940B2

Reaction notes

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