Potassium Carbonate → 6-Amino-7-cyclopropyl-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one

HRID 518984ノート

反応式

HRID 518984 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][C:15]=1Br)[O:12][CH2:11][C:10]1[N:5]2[CH:6]([CH3:18])[C:7](=[O:17])[NH:8][N:9]=1.[CH:19]1(B(O)O)[CH2:21][CH2:20]1.C([O-])([O-])=O.[K+].[K+]>O.O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[NH2:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][C:15]=1[CH:19]1[CH2:21][CH2:20]1)[O:12][CH2:11][C:10]1[N:5]2[CH:6]([CH3:18])[C:7](=[O:17])[NH:8][N:9]=1

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 2760897Cyclopropylboronic acidHCID 86727335HCID 86727335、化合物

生成物 1

HCID 867273366-Amino-7-cyclopropyl-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one収率 54%

試薬・触媒・溶媒 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
130 °C

実験手順

A mixture of 6-amino-7-bromo-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (0.500 g, 1.607 mmol), cyclopropylboronic acid (1.38 g, 16.07 mmol), K2CO3 (0.888 g, 6.43 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.262 g, 0.321 mmol) in water (10 mL) and dioxane (60 mL) was heated at 130° C. for 2 h. The reaction mixture was cooled to ambient temperature and the solution was concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 30-100% EtOAc in petroleum ether) to give 6-amino-7-cyclopropyl-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (0.235 g, 0.863 mmol, 54%). 1H NMR (DMSO-d6, 400 MHz): δ 10.71 (s 1H), 6.50 (s, 1H), 6.45 (s, 1H), 4.75 (brs, 2H), 4.45 (m, 3H), 1.60 (m, 1H), 1.31 (d, J=6.8 Hz, 3H), 0.83 (m, 2H), 0.46 (m, 2H).

後処理

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. concentrationthe solution was concentrated in vacuo
  3. customThe residue was purified by column chromatography on silica gel (eluting with 30-100% EtOAc in petroleum ether)

出典と根拠

ORDレコード
ord-c7b2b8d3dde5497d87e42d64abe14383
出典データセット
uspto-grants-2015_08
特許番号
US09115151B2

反応ノート

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