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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
Notes
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Reaction equation

HRID 519224 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-af382d10bb8645c5a5a8bb948b790c1c
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09115151B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes