Methyl Acrylate → HCID 66919139, compound

HRID 2354229Notes

Reaction equation

HRID 2354229 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:20]1([NH:23][C:24](=[O:44])[C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[C:27]([N:32]3[C:41](=[O:42])[C:40]4[C:35](=[CH:36][CH:37]=[C:38](I)[CH:39]=4)[N:34]=[CH:33]3)[CH:26]=2)[CH2:22][CH2:21]1.[C:45]([O:49][CH3:50])(=[O:48])[CH:46]=[CH2:47].C(N(CC)CC)C>O1CCCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:20]1([NH:23][C:24]([C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[C:27]([N:32]3[C:41](=[O:42])[C:40]4[C:35](=[CH:36][CH:37]=[C:38](/[CH:47]=[CH:46]/[C:45]([O:49][CH3:50])=[O:48])[CH:39]=4)[N:34]=[CH:33]3)[CH:26]=2)=[O:44])[CH2:22][CH2:21]1

Participants

7

Reactant 4

HCID 7294Methyl AcrylateHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 11487616HCID 11487616, compound

Product 1

HCID 66919139HCID 66919139, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Palladium acetate (0.02 g) and triphenylphosphine (0.038 g) was added to a stirred mixture N-cyclopropyl-3-(6-iodo-4-oxoquinazolin-3(4H)-yl)-4-methylbenzamide (0.20 g), methyl acrylate (0.4 ml) and triethylamine (0.63 ml) in anhydrous tetrahydrofuran (15 ml) under an argon atmosphere. The mixture was heated to 60° C. and stirred for 2 hours. The reaction mixture was evaporated, dissolved in ethyl acetate (100 ml) and washed with water (100 ml) and brine (100 ml). The organic phase was dried (magnesium sulphate) and evaporated and the residue purified by column chromatography on a silica column using initially iso-hexane and then a 1:1 mixture of iso-hexane and ethyl acetate as eluent. There was thus obtained the title compound (0.14 g); NMR Spectrum: (DMSOd6) 0.57 (m, 2H), 0.70 (m, 2H), 2.17 (s, 3H), 2.86 (m, 1H), 3.76 (s, 3H), 6.80 (d, 1H), 7.55 (m, 2H), 7.63 (m, 1H), 7.86 (m, 2H), 8.31 (m, 1H), 8.37 (s, 1H), 8.45 (m, 2H); Mass Spectrum: M+H+ 404.

Workup

  1. customThe reaction mixture was evaporated
  2. dissolutiondissolved in ethyl acetate (100 ml)
  3. washwashed with water (100 ml) and brine (100 ml)
  4. dry with materialThe organic phase was dried (magnesium sulphate)
  5. customevaporated
  6. customthe residue purified by column chromatography on a silica column
  7. additiona 1:1 mixture of iso-hexane and ethyl acetate as eluent

Sources & evidence

ORD record
ord-fe7779f0c8224343a516fde9cb130226
Source dataset
uspto-grants-2010_07
Patent number
US07750154B2

Reaction notes

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