Cesium carbonate → HCID 131722505, compound

HRID 324411Notes

Reaction equation

HRID 324411 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]2[CH:16]([C:17]3[C:18](=[O:24])[NH:19][C:20](=[O:23])[NH:21][CH:22]=3)[C:11]3[N:12]=[C:13]([CH3:15])[O:14][C:10]=3[CH:9]=[CH:8][C:7]=2[CH:25]=1)[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Cl.Cl[CH2:34][C:35]1[CH:36]=[C:37]([CH:43]=[C:44]([CH2:46][N:47]2[CH:51]=[CH:50][N:49]=[CH:48]2)[CH:45]=1)[C:38]([O:40][CH2:41][CH3:42])=[O:39]>CS(C)=O>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]2[CH:16]([C:17]3[C:18](=[O:24])[NH:19][C:20](=[O:23])[N:21]([CH2:34][C:35]4[CH:36]=[C:37]([CH:43]=[C:44]([CH2:46][N:47]5[CH:51]=[CH:50][N:49]=[CH:48]5)[CH:45]=4)[C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH:22]=3)[C:11]3[N:12]=[C:13]([CH3:15])[O:14][C:10]=3[CH:9]=[CH:8][C:7]=2[CH:25]=1)[CH3:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 70113435(+/-)-5-(7-Ethyl-2-methyl-4H-benzo[5,6]cyclohepta[1,2-d]oxazol-4-yl)-2,4(1H,3H)-pyrimidinedioneHCID 131722506HCID 131722506, compound

Product 1

HCID 131722505HCID 131722505, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of the product of example 3 step (vii) (2.5 g) in dry dimethylsulphoxide (30 ml) was treated with cesium carbonate (10 g) with stirring. After 20 min a solution of the product of step (ii) (1.5 g) in dimethylsulphoxide (10 ml) was added dropwise over 2 min. After 1.5 hours the reaction mixture was quenched with saturated brine and the product extracted into ethyl acetate. The organic phase was dried (MgSO4) and the solvent was evaporated under reduced pressure to leave a brown gum. Column chromatography eluting with 10% methanol in ethyl acetate containing 1% triethylamine gave the product as a glass.

Workup

  1. customAfter 1.5 hours the reaction mixture was quenched with saturated brine
  2. extractionthe product extracted into ethyl acetate
  3. dry with materialThe organic phase was dried (MgSO4)
  4. customthe solvent was evaporated under reduced pressure
  5. customto leave a brown gum
  6. washColumn chromatography eluting with 10% methanol in ethyl acetate containing 1% triethylamine

Sources & evidence

ORD record
ord-8f4fcf77c863405b8a2ca7a37919b3cb
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Reaction notes

Loading…