Methyl morpholine oxide → HCID 18366609, compound

HRID 379591Notes

Reaction equation

HRID 379591 reaction equation
[Br:1][C:2]1[C:10]2[C:9](=[O:11])[N:8]([CH3:12])[C:7](=[O:13])[N:6]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:5]=2[S:4][C:3]=1[CH:18]([OH:29])[C:19]1[N:23]([CH3:24])[C:22]2[CH:25]=[CH:26][CH:27]=[CH:28][C:21]=2[N:20]=1.C[N+]1([O-])CCOCC1>ClCCl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[Br:1][C:2]1[C:10]2[C:9](=[O:11])[N:8]([CH3:12])[C:7](=[O:13])[N:6]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:5]=2[S:4][C:3]=1[C:18]([C:19]1[N:23]([CH3:24])[C:22]2[CH:25]=[CH:26][CH:27]=[CH:28][C:21]=2[N:20]=1)=[O:29]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 18366606HCID 18366606, compound

Product 1

HCID 18366609HCID 18366609, compoundYield 58.8%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Prepared according to the method described in Example 37 step c from 5-bromo-6-[hydroxy(1-methyl-1H-benzimidazol-2-yl)methyl]-3-methyl-1-(2-methylpropyl)-thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (5.0 g), 4-methylmorpholine-N-oxide (1.84 g), powdered 4 Å sieves (5.0 g) and tetra-n-propyl-ammonium perruthenate (0.18 g) in dry dichloromethane (170 ml) with stirring at room temperature for 24 hours. After work up, the residue was purified by column chromatography over silica eluting with a gradient of 0-2% ethanol in dichloromethane to give the subtitle compound as a yellow powder (2.93 g).

Workup

  1. customPrepared
  2. customAfter work up, the residue was purified by column chromatography over silica eluting with a gradient of 0-2% ethanol in dichloromethane

Sources & evidence

ORD record
ord-da46f104d2564f07980f85e01e57ed5c
Source dataset
uspto-grants-2001_10
Patent number
US06300334B1

Reaction notes

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