Methyl morpholine oxide → HCID 21941669, compound

HRID 2216308Notes

Reaction equation

HRID 2216308 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:12]2[CH:17]([CH2:18][C:19]3[C:24]([CH3:25])=[CH:23][C:22]([CH3:26])=[CH:21][C:20]=3[CH3:27])[NH:16][C:15]([CH3:28])=[N:14][CH:13]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.C[N+]1([O-])CCOCC1>CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:12]2[C:17]([CH2:18][C:19]3[C:20]([CH3:27])=[CH:21][C:22]([CH3:26])=[CH:23][C:24]=3[CH3:25])=[N:16][C:15]([CH3:28])=[N:14][CH:13]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 178492802HCID 178492802, compound

Product 1

HCID 21941669HCID 21941669, compoundYield 82.3%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture 5-(4-methoxy-benzenesulfonyl)-2-methyl-6-(2,4,6-trimethylbenzyl)-1,6-dihydro-pyrimidine (167 mg, 0.42 mmol), NMO (74 mg, 0.63 mmol), TPAP (29 mg, 0.084 mmol), 4 Å molecular sieves (200 mg) and CH2Cl2 (5 mL) was stirred under N2 at room temperature for 2 h. The mixture was filtered through a pad of silica gel and the filtrate was concentrated in vacuo. The residue was purified by chromatography on silica gel (67:33 hexanes/EtOAc) to provide the target compound (137 mg, 82%) as a light yellow solid: mp 150–152° C.; 1H NMR (500 MHz, CDCl3) δ 9.22 (s, 1H), 7.93 (d, J=8.9 Hz, 2H), 7.06 (d, J=8.9 Hz, 2H), 6.83 (s, 2H), 4.25 (s, 2H), 3.91 (s, 3H), 2.59 (s, 3H), 2.29 (s, 3H), 1.91 (s, 6H); ESI MS m/z 397 [(M+H)+, calcd for C22H25N2O3S, 397.2].

Workup

  1. filtrationThe mixture was filtered through a pad of silica gel
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by chromatography on silica gel (67:33 hexanes/EtOAc)

Sources & evidence

ORD record
ord-6509deb9b9e64dc8af01a8bdd5f4a6e8
Source dataset
uspto-grants-2006_09
Patent number
US07112585B2

Reaction notes

Loading…