Triethylamine → methyl 3-[6-[(1E)-3-tert-butoxy-3-oxoprop-1-en-1-yl]-4-oxoquinazolin-3(4H)-yl]-4-methylbenzoate

HRID 641988ノート

反応式

HRID 641988 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]([C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][C:21]=1[CH3:22])[C:15]([O:17][CH3:18])=[O:16])[C:5]2=[O:23].[C:24]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])(=[O:27])[CH:25]=[CH2:26].C(N(CC)CC)C>CN(C=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].CC(P(C(C)(C)C)C1[CH-]C=CC=1)(C)C.C1C=CC([C-]2C(C3C=CC=CC=3)=C(C3C=CC=CC=3)C(C3C=CC=CC=3)=C2C2C=CC=CC=2)=CC=1.[Fe+2]>[C:29]([O:28][C:24](=[O:27])/[CH:25]=[CH:26]/[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]([C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][C:21]=1[CH3:22])[C:15]([O:17][CH3:18])=[O:16])[C:5]2=[O:23])([CH3:32])([CH3:31])[CH3:30]

参加物

7

反応物 3

HCID 8471TriethylamineHCID 15458tert-Butyl acrylateHCID 66919066Methyl 3-(6-bromo-4-oxoquinazolin-3(4H)-yl)-4-methylbenzoate

生成物 1

HCID 68511776methyl 3-[6-[(1E)-3-tert-butoxy-3-oxoprop-1-en-1-yl]-4-oxoquinazolin-3(4H)-yl]-4-methylbenzoate

試薬・触媒・溶媒 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium触媒HCID 12024214Ditert-butyl(cyclopenta-1,3-dien-1-yl)phosphane;iron(2+);(2,3,4,5-tetraphenylcyclopenta-1,4-dien-1-yl)benzene触媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of methyl 3-(6-bromo-4-oxoquinazolin-3(4H)-yl)-4-methylbenzoate (5.00 g), bis(dibenzylideneacetone)palladium (0.19 g) and 1,2,3,4,5-pentaphenyl-1-(di-tert-butylphosphino)ferrocene (0.47 g) in anhydrous DMF (30 ml) under an argon atmosphere was added tert-butyl acrylate (4.3 ml) followed by triethylamine (4.5 ml). The reaction mixture was stirred at room temperature for 72 hours, then heated at 100° C. for 5 hours and poured onto brine. The resulting mixture was extracted with ethyl acetate and the combined organic layers were washed with water, dried (magnesium sulphate) and concentrated to give methyl 3-[6-[(1E)-3-tert-butoxy-3-oxoprop-1-en-1-yl]-4-oxoquinazolin-3(4H)-yl]-4-methylbenzoate as a solid (5.83 g). NMR Spectrum: (DMSOd6) 1.51 (s, 9H), 2.20 (s, 3H), 3.88 (s, 3H), 6.67 (d, 1H), 7.63 (d, 1H), 7.75 (d, 1H), 7.77 (d, 1H), 8.04 (m, 2H), 8.28 (m, 1H), 8.34 (s, 1H), 8.40 (d, 1H); Mass Spectrum: M+H+ 421.

後処理

  1. temperatureheated at 100° C. for 5 hours
  2. additionpoured onto brine
  3. extractionThe resulting mixture was extracted with ethyl acetate
  4. washthe combined organic layers were washed with water
  5. dry with materialdried (magnesium sulphate)
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-c183c5e42d1140128b2ba6137be62b91
出典データセット
uspto-grants-2010_04
特許番号
US07696215B2

反応ノート

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