Cesium carbonate → 1-[2,6-Dichloropyrimidin-4-yl]-5-[2,8-dimethyl-5H-dibenzo[a,d]cyclohepten-5-yl]-2,4(1H,3H)-pyrimidinedione

HRID 1871985Notes

Reaction equation

HRID 1871985 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:7][C:8]1[CH:31]=[CH:30][C:11]2[CH:12]([C:22]3[C:23](=[O:29])[NH:24][C:25](=[O:28])[NH:26][CH:27]=3)[C:13]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:14]=3[CH:15]=[CH:16][C:10]=2[CH:9]=1.[Cl:32][C:33]1[N:38]=[C:37](Cl)[CH:36]=[C:35]([Cl:40])[N:34]=1>CN1CCCC1=O>[Cl:32][C:33]1[N:38]=[C:37]([N:26]2[CH:27]=[C:22]([CH:12]3[C:13]4[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:14]=4[CH:15]=[CH:16][C:10]4[CH:9]=[C:8]([CH3:7])[CH:31]=[CH:30][C:11]3=4)[C:23](=[O:29])[NH:24][C:25]2=[O:28])[CH:36]=[C:35]([Cl:40])[N:34]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 773782,4,6-TrichloropyrimidineHCID 221172135-(2,8-Dimethyl-5h-dibenzo[a,d]cyclohepten-5-yl)-2,4(1h,3h)-pyrimidinedione

Product 1

HCID 186897721-[2,6-Dichloropyrimidin-4-yl]-5-[2,8-dimethyl-5H-dibenzo[a,d]cyclohepten-5-yl]-2,4(1H,3H)-pyrimidinedione

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Cesium carbonate (5 g) was added to a solution of the product of example 8 step (i) (5 g) in 1-methyl-2-pyrrolidinone (50 ml). After 5 minutes 2,4,6-trichloropyrimidine (2.8 g) was added. After 2 hours the reaction was partitioned between brine and ethyl acetate. The organic phase was washed with water, dried (MgSO4) and evaporated under reduced pressure. Purification was by chromatography eluting with 30% ethyl acetate in toluene. Yield 2.9 g.

Workup

  1. customAfter 2 hours the reaction was partitioned between brine and ethyl acetate
  2. washThe organic phase was washed with water
  3. dry with materialdried (MgSO4)
  4. customevaporated under reduced pressure
  5. customPurification
  6. washeluting with 30% ethyl acetate in toluene

Sources & evidence

ORD record
ord-848f047d93254a34847dfc85bc912591
Source dataset
uspto-grants-2000_08
Patent number
US06107297

Reaction notes

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