Triethylamine → HCID 86755646, compound

HRID 1871965Notes

Reaction equation

HRID 1871965 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[CH:7]1[C:17]2[CH:16]=[CH:15][C:14]3[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=3[CH:12]([C:22]3[C:23](=[O:29])[NH:24][C:25](=[O:28])[NH:26][CH:27]=3)[C:11]=2[CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C.Cl[CH2:38][C:39]1[N:44]=[C:43]([C:45]([O:47][CH3:48])=[O:46])[CH:42]=[CH:41][CH:40]=1>CS(C)=O>[CH:7]1[C:17]2[CH:16]=[CH:15][C:14]3[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=3[CH:12]([C:22]3[C:23](=[O:29])[NH:24][C:25](=[O:28])[N:26]([CH2:38][C:39]4[N:44]=[C:43]([C:45]([O:47][CH3:48])=[O:46])[CH:42]=[CH:41][CH:40]=4)[CH:27]=3)[C:11]=2[CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10796Cesium carbonateHCID 110986755-(5h-Dibenzo[a,d]cyclohepten-5-yl)-2,4(1h,3h)-pyrimidinedioneHCID 53404482Methyl 6-(chloromethyl)pyridine-2-carboxylate

Product 1

HCID 86755646HCID 86755646, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Cesium carbonate (1.63 g) was added to a stirred solution of the product of step (iv) (1.5 g) in dimethylsulphoxide (20 ml). After 15 minutes triethylamine (0.71 ml) was added followed by the product from step (ii) (1.11 g). The mixture was stirred at room temperature for 4 hours and partitioned between ethyl acetate and water. The organic phase was dried (MgSO4) and evaporated. Purification was by chromatography eluting with 5% methanol in chloroform. Yield 1.86 g.

Workup

  1. custompartitioned between ethyl acetate and water
  2. dry with materialThe organic phase was dried (MgSO4)
  3. customevaporated
  4. customPurification
  5. washeluting with 5% methanol in chloroform

Sources & evidence

ORD record
ord-4ec03a1821244395816ee0123f338f18
Source dataset
uspto-grants-2000_08
Patent number
US06107297

Reaction notes

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