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Tetrahydrofuran → (6,6-Dioxo-5,6-dihydro-6lambda*6*-thia-4,5-diaza-chrysen-12-yl)-morpholin-4-yl-methanone

HRID 513793
Notes
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Reaction equation

HRID 513793 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Br[C:8]1[CH:9]=[C:10]2[C:19](=[C:20]3[C:25]=1[CH:24]=[CH:23][CH:22]=[N:21]3)[NH:18][S:17](=[O:27])(=[O:26])[C:16]1[C:11]2=[CH:12][CH:13]=[CH:14][CH:15]=1.C1CCN2C(=NCCC2)CC1.C1C[O:42][CH2:41]C1>>[O:26]=[S:17]1(=[O:27])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]2[C:19](=[C:20]3[C:25](=[C:8]([C:41]([N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)=[O:42])[CH:9]=2)[CH:24]=[CH:23][CH:22]=[N:21]3)[NH:18]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8083MorpholineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 1675994412-bromo-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide

Product 1

HCID 68183198(6,6-Dioxo-5,6-dihydro-6lambda*6*-thia-4,5-diaza-chrysen-12-yl)-morpholin-4-yl-methanoneYield 6%

Conditions

Temperature
150 °C

Procedure

Morpholine was added to a suspension of 12-bromo-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide 545 (100 mg, 0.28 mmol), Hermann's palladacycle (13 mg, 14 μmol), Mo(CO)6 (73 mg, 0.28 mmol), DBU (126 mg, 0.83 mmol) and THF (2 ml) in a microwave vessel. The vessel was sealed under air and the mixture was heated in the microwave at 150° C. for 15 min. After cooling, the mixture was concentrated in vacuo. The residue was diluted with MeOH (2 ml), filtered and the filtrate was purified by preparative HPLC (acidic conditions 1) to give the title compound (6 mg, 6%).

Workup

  1. customThe vessel was sealed under air
  2. temperatureAfter cooling
  3. concentrationthe mixture was concentrated in vacuo
  4. additionThe residue was diluted with MeOH (2 ml)
  5. filtrationfiltered
  6. customthe filtrate was purified by preparative HPLC (acidic conditions 1)

Sources & evidence

ORD record
ord-8477ea60869d417f8b7dfe3ed7fe0dcd
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09102688B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes