Cesium carbonate → 3-[[5-{5H-Dibenzo[a,d]cyclohepten-5-yl}-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl]methyl]benzoic acid, methyl ester

HRID 1531914Notes

Reaction equation

HRID 1531914 reaction equation
[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[CH:6]([C:16]3[C:17](=[O:23])[NH:18][C:19](=[O:22])[NH:20][CH:21]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:30][O:31][C:32](=[O:41])[C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([CH2:39]Br)[CH:34]=1>CS(C)=O>[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[CH:6]([C:16]3[C:17](=[O:23])[NH:18][C:19](=[O:22])[N:20]([CH2:39][C:35]4[CH:34]=[C:33]([CH:38]=[CH:37][CH:36]=4)[C:32]([O:31][CH3:30])=[O:41])[CH:21]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 517981Methyl 3-(bromomethyl)benzoateHCID 110986755-(5h-Dibenzo[a,d]cyclohepten-5-yl)-2,4(1h,3h)-pyrimidinedione

Product 1

HCID 1317224273-[[5-{5H-Dibenzo[a,d]cyclohepten-5-yl}-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl]methyl]benzoic acid, methyl ester

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a solution of the product from step (ii) (0.7 g) in DMSO (5 ml) was added cesium carbonate (0.75 g). After 5 minutes a solution of 3-bromomethylbenzoic acid methyl ester (0.53 g) in DMSO (5 ml) was added. The mixture was stirred at room temperature for 20 minutes and partitioned between ethyl acetate and water. The organic phase was washed with water and brine, dried (MgSO4) and evaporated. Purified by chromatography eluting with 30% ethyl acetate in isohexane. Yield 0.34 g.

Workup

  1. custompartitioned between ethyl acetate and water
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customPurified by chromatography
  6. washeluting with 30% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-77bd0834d5da4bb59c80f667ebf78561
Source dataset
uspto-grants-2001_03
Patent number
US06200981B1

Reaction notes

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