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Water → 6-Bromo-4,7-dimethyl-2-(2-trimethylsilanyl-ethoxymethyl)-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one

HRID 519224
ノート
印刷プレビュー

反応式

HRID 519224 の反応式
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]2[C:15](=[CH:16][C:17]=1[CH3:18])[O:14][CH2:13][C:12]1[N:7]2[CH:8]([CH3:20])[C:9](=[O:19])[NH:10][N:11]=1.Cl[CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27].O>CN(C=O)C>[Br:3][C:4]1[CH:5]=[C:6]2[C:15](=[CH:16][C:17]=1[CH3:18])[O:14][CH2:13][C:12]1[N:7]2[CH:8]([CH3:20])[C:9](=[O:19])[N:10]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[N:11]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 867276286-Bromo-4,7-dimethyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one

生成物 1

HCID 867276296-Bromo-4,7-dimethyl-2-(2-trimethylsilanyl-ethoxymethyl)-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one収率 79%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a suspension of NaH (60%, 0.387 g, 9.67 mmol) in DMF (15 mL) was added 6-bromo-4,7-dimethyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (2.0 g, 6.45 mmol) in portions and the reaction mixture was stirred at 0° C. for 0.5 h. (2-(Chloromethoxy)ethyl)trimethylsilane (1.613 g, 9.67 mmol) was added and the reaction mixture was warmed to ambient temperature and stirred for 2 h. Water (100 mL) was added and the aqueous solution was extracted with EtOAc (3×50 mL). The combined organic phase was washed with brine (100 mL) and dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 30% EtOAc in petroleum ether) to give 6-bromo-4,7-dimethyl-2-(2-trimethylsilanyl-ethoxymethyl)-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one as solid (2.24 g, 79%). 1H NMR (DMSO-d6, 400 MHz): δ 7.52 (s, 1H), 7.12 (s, 1H), 5.01 (m, 2H), 4.95 (m, 1H), 4.68 (s, 2H), 3.60 (m, 2H), 2.28 (s, 3H), 1.32 (m, 3H), 0.89 (m, 2H), 0.00 (s, 9H).

後処理

  1. additionwas added
  2. extractionthe aqueous solution was extracted with EtOAc (3×50 mL)
  3. washThe combined organic phase was washed with brine (100 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography on silica gel (eluting with 30% EtOAc in petroleum ether)

出典と根拠

ORDレコード
ord-af382d10bb8645c5a5a8bb948b790c1c
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09115151B2

反応ノート

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