Cesium carbonate → (+/-)-N-[4-[5-{2-Ethyl-8-methyl-5H-dibenzo[a,d]cyclohepten-5-yl}-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl]pyrimidin-2-yl]-N-methylglycine, methyl ester

HRID 1871990Notes

Reaction equation

HRID 1871990 reaction equation
F[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([N:8]([CH3:14])[CH2:9][C:10]([O:12][CH3:13])=[O:11])[N:3]=1.[CH2:15]([C:17]1[CH:40]=[CH:39][C:20]2[CH:21]([C:31]3[C:32](=[O:38])[NH:33][C:34](=[O:37])[NH:35][CH:36]=3)[C:22]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][C:23]=3[CH:24]=[CH:25][C:19]=2[CH:18]=1)[CH3:16].C(=O)([O-])[O-].[Cs+].[Cs+]>CN1CCCC1=O>[CH2:15]([C:17]1[CH:40]=[CH:39][C:20]2[CH:21]([C:31]3[C:32](=[O:38])[NH:33][C:34](=[O:37])[N:35]([C:2]4[CH:7]=[CH:6][N:5]=[C:4]([N:8]([CH3:14])[CH2:9][C:10]([O:12][CH3:13])=[O:11])[N:3]=4)[CH:36]=3)[C:22]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][C:23]=3[CH:24]=[CH:25][C:19]=2[CH:18]=1)[CH3:16]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 22117281(+/-)-5-[2-Ethyl-8-methyl-5H-dibenzo[a,d]cyclohepten-5-yl]-2,4(1H,3H)-pyrimidinedioneHCID 131721952N-[4-Fluoropyrimidin-2-yl]-N-methylglycine, methyl ester

Product 1

HCID 131721953(+/-)-N-[4-[5-{2-Ethyl-8-methyl-5H-dibenzo[a,d]cyclohepten-5-yl}-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl]pyrimidin-2-yl]-N-methylglycine, methyl ester

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of the product of step (i) (0.68 g), and the product of example 15 step (vii) (2.35 g) was stirred with cesium carbonate (2.22 g) in 1-methyl-2-pyrrolidinone (20 ml) at 70-80° C. for 4 hours. The reaction mixture was partitioned between ethyl acetate and brine. The organic layer was dried (MgSO4) and evaporated under reduced pressure. The residue was purified by chromatography eluting with ethyl acetate in toluene. Yield 0.57 g.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and brine
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customevaporated under reduced pressure
  4. customThe residue was purified by chromatography
  5. washeluting with ethyl acetate in toluene

Sources & evidence

ORD record
ord-ca59f79ee1fc4f0a964c9d4dbab2540b
Source dataset
uspto-grants-2000_08
Patent number
US06107297

Reaction notes

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