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Butyl vinyl ether → 1-(6,6-Dioxo-5,6-dihydro-6lambda*6*-thia-4,5-diaza-chrysen-12-yl)-ethanone

HRID 513796
ノート
印刷プレビュー

反応式

HRID 513796 の反応式
[CH:1]([O:3]CCCC)=[CH2:2].C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].Br[C:44]1[CH:45]=[C:46]2[C:55](=[C:56]3[C:61]=1[CH:60]=[CH:59][CH:58]=[N:57]3)[NH:54][S:53](=[O:63])(=[O:62])[C:52]1[C:47]2=[CH:48][CH:49]=[CH:50][CH:51]=1>C1COCC1.Cl.CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2].CN(C=O)C.O>[O:62]=[S:53]1(=[O:63])[C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[C:46]2[C:55](=[C:56]3[C:61](=[C:44]([C:1](=[O:3])[CH3:2])[CH:45]=2)[CH:60]=[CH:59][CH:58]=[N:57]3)[NH:54]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

10

反応物 4

HCID 8108Butyl vinyl etherHCID 11430Potassium CarbonateHCID 812191,3-Bis(diphenylphosphino)propaneHCID 1675994412-bromo-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide

生成物 1

HCID 681830641-(6,6-Dioxo-5,6-dihydro-6lambda*6*-thia-4,5-diaza-chrysen-12-yl)-ethanone収率 30.5%

試薬・触媒・溶媒 5

HCID 167845
palladium(II) acetate
触媒
HCID 313Hydrochloric Acid溶媒
HCID 8028Tetrahydrofuran溶媒
HCID 8857Ethyl Acetate溶媒
HCID 21962138N,N-Dimethylformamide--water (1/1)溶媒

反応条件

温度
90 °C

実験手順

A solution of DMF/H2O (4:1) was de-gassed for 15 min. DMF/H2O (4:1, 6 ml) and 1-vinyloxy-butane (0.59 ml, 4.53 mmol) were added to a mixture of Pd(OAc)2 (6 mg, 26 μmol), 1,3-bis(diphenylphosphino)propane (24 mg, 57 K2CO3 (150 mg, 1.01 mmol), 12-bromo-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide 545 (370 mg, 0.91 mmol), under nitrogen. The mixture was heated at 90° C. for 2.5 h in the microwave. After cooling, the reaction was diluted with THF (2 ml) and 1M HCl (2 ml) and the mixture was stirred for 18 h. The mixture was further diluted with EtOAc (10 ml) and washed with water (10 ml, ×3). The precipitate formed during work-up was collected by filtration of the organic and aqueous phases and was found to be the title compound (140 mg, 40%). The organic phase was dried (Na2SO4) and concentrated in vacuo. The residue was triturated from MeOH to give the title compound (90 mg, 24%) which was used in the next step without further purification.

後処理

  1. customA solution of DMF/H2O (4:1) was de-gassed for 15 min
  2. temperatureAfter cooling
  3. washwashed with water (10 ml, ×3)
  4. customThe precipitate formed during work-up
  5. filtrationwas collected by filtration of the organic and aqueous phases
  6. dry with materialThe organic phase was dried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was triturated from MeOH

出典と根拠

ORDレコード
ord-9cf66d933baa40a1ba1220de3821cd77
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09102688B2

反応ノート

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