Methyl morpholine oxide → HCID 58985751, compound

HRID 1169799Notes

Reaction equation

HRID 1169799 reaction equation
[CH2:1]([O:3][C:4]([N:6]=[S:7]([C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]2[N:22]=[C:21]([NH:23][CH2:24][CH2:25][CH:26]([OH:28])[CH3:27])[C:20]([C:29]3[S:30][CH:31]=[CH:32][CH:33]=3)=[CH:19][N:18]=2)=[CH:12][CH:11]=1)([CH3:9])=[O:8])=[O:5])[CH3:2].C[N+]1([O-])CCOCC1>ClCCl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH2:1]([O:3][C:4]([N:6]=[S:7]([C:10]1[CH:11]=[CH:12][C:13]([NH:16][C:17]2[N:22]=[C:21]([NH:23][CH2:24][CH2:25][C:26](=[O:28])[CH3:27])[C:20]([C:29]3[S:30][CH:31]=[CH:32][CH:33]=3)=[CH:19][N:18]=2)=[CH:14][CH:15]=1)([CH3:9])=[O:8])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 58985591HCID 58985591, compound

Product 1

HCID 58985751HCID 58985751, compound

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

(RS)—N(ethoxycarbonyl)-(4-{[4-{(3-hydroxybutyl)amino}-5-(thiophen-2-yl)-pyrimidin-2-yl]amino}phenyl)-S-methylsulfoximide (169 mg, 0.35 mmol) is dissolved in dichloromethane (15 ml) and N-methylmorpholin-N-oxid (123 mg, 1.05 mmol) and molecular sieve (4 A, 496 mg) is added. The mixture is stirred for 15 min at RT. Then tetrapropylammoniumperruthenat (6.3 mg, 0.018 mmol) is added, the reaction mixture is stirred for 24 h at RT. Additional tetrapropylammoniumperruthenat (10.4 mg, 0.03 mmol) is added and the reaction mixture is stirred for 24 h at RT. For workup the mixture is filtered through celite and washed with dichloromethane. The solvent is evaporated resulting in the crude product which is purified by column chromatography: 39 mg, 23%.

Workup

  1. stirringthe reaction mixture is stirred for 24 h at RT
  2. stirringthe reaction mixture is stirred for 24 h at RT
  3. filtrationFor workup the mixture is filtered through celite
  4. washwashed with dichloromethane
  5. customThe solvent is evaporated

Sources & evidence

ORD record
ord-84f3b450524a4daea17e35da7fdfbcba
Source dataset
uspto-grants-2010_11
Patent number
US07825128B2

Reaction notes

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