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

HRID 641988노트

반응식

HRID 641988 반응식
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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium촉매HCID 12024214Ditert-butyl(cyclopenta-1,3-dien-1-yl)phosphane;iron(2+);(2,3,4,5-tetraphenylcyclopenta-1,4-dien-1-yl)benzene촉매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c183c5e42d1140128b2ba6137be62b91
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696215B2

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