Methanol → HCID 66918943, compound

HRID 2354228Notes

Reaction equation

HRID 2354228 reaction equation
[CH:1]1([NH:4][C:5](=[O:30])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([N:13]3[C:22](=[O:23])[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([C:24]#[C:25][CH2:26][N:27]([CH3:29])[CH3:28])[CH:20]=4)[N:15]=[CH:14]3)[CH:7]=2)[CH2:3][CH2:2]1.CO>[Pd].C(O)C>[CH:1]1([NH:4][C:5](=[O:30])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([N:13]3[C:22](=[O:23])[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([CH2:24][CH2:25][CH2:26][N:27]([CH3:28])[CH3:29])[CH:20]=4)[N:15]=[CH:14]3)[CH:7]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 887MethanolHCID 66919070HCID 66919070, compound

Product 1

HCID 66918943HCID 66918943, compoundYield 69.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N-Cyclopropyl-3-[6-[3-(dimethylamino)prop-1-yn-1-yl]-4-oxoquinazolin-3(4H)-yl]-4-methylbenzamide (0.097 g) and 10% Palladium on carbon (0.01 g) were stirred in ethanol (2 ml) and methanol (0.5 ml) under an atmosphere of hydrogen for 2 hours. The catalyst was removed by filtration through diatomaceous earth (Celite®) and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on a silica column eluting with 10% methanol/ethyl acetate followed by 10% methanol/ethyl acetate+1% aqueous ammonia solution to give the title compound (0.068 g) as a white foam solid; NMR Spectrum: (DMSOd6) 0.56 (m, 2H), 0.70 (m, 2H), 1.78 (m, 2H), 2.15 (s, 9H), 2.23 (t, 2H), 2.78 (t, 2H), 2.86 (m, 1H), 7.53 (d, 1H), 7.71 (d, 1H), 7.78 (d, 1H), 7.83 (s, 1H), 7.91 (d, 1H), 8.02 (s, 1H), 8.25 (s, 1H), 8.42 (d, 1H); Mass Spectrum: M+H+ 405.

Workup

  1. customThe catalyst was removed by filtration through diatomaceous earth (Celite®)
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by column chromatography on a silica column
  4. washeluting with 10% methanol/ethyl acetate

Sources & evidence

ORD record
ord-0d434cb1534c4789b4ca6fe65aa92495
Source dataset
uspto-grants-2010_07
Patent number
US07750154B2

Reaction notes

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