Cesium carbonate → 2-[5-{2,8-Dimethyl-5H-dibenzo[a,d]cyclohepten-5-yl}-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl]-4-[[[1,1-dimethylethoxy]carbonylmethyl]amino]-5-pyrimidinecarboxylic acid, methyl ester

HRID 1871987Notes

Reaction equation

HRID 1871987 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C:5]([C:17]([O:19][CH3:20])=[O:18])=[CH:4][N:3]=1.[CH3:21][C:22]1[CH:45]=[CH:44][C:25]2[CH:26]([C:36]3[C:37](=[O:43])[NH:38][C:39](=[O:42])[NH:40][CH:41]=3)[C:27]3[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][C:28]=3[CH:29]=[CH:30][C:24]=2[CH:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH3:21][C:22]1[CH:45]=[CH:44][C:25]2[CH:26]([C:36]3[C:37](=[O:43])[NH:38][C:39](=[O:42])[N:40]([C:2]4[N:7]=[C:6]([NH:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C:5]([C:17]([O:19][CH3:20])=[O:18])=[CH:4][N:3]=4)[CH:41]=3)[C:27]3[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][C:28]=3[CH:29]=[CH:30][C:24]=2[CH:23]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 221172135-(2,8-Dimethyl-5h-dibenzo[a,d]cyclohepten-5-yl)-2,4(1h,3h)-pyrimidinedioneHCID 867556542-Chloro-4-[[[1,1-dimethylethoxy]carbonylmethyl]amino]-5-pyrimidinecarboxylic acid, methyl ester

Product 1

HCID 867556552-[5-{2,8-Dimethyl-5H-dibenzo[a,d]cyclohepten-5-yl}-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl]-4-[[[1,1-dimethylethoxy]carbonylmethyl]amino]-5-pyrimidinecarboxylic acid, methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the product of step (ii) (0.52 g), the product of example 8 step (i) (0.5 g) and cesium carbonate (0.49 g) in dimethylformamide (15 ml) was heated at 70° C. After 3 hours, the reaction mixture was partitioned between 1M HCl and ethyl acetate. The organic phase was washed with water, dried (MgSO4) and evaporated under reduced pressure. Purification was by chromatography eluting with 3% methanol in chloroform. Yield 0.47 g.

Workup

  1. customthe reaction mixture was partitioned between 1M HCl 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 3% methanol in chloroform

Sources & evidence

ORD record
ord-32bbe3c4cd604d43ab12f69eb4092f6c
Source dataset
uspto-grants-2000_08
Patent number
US06107297

Reaction notes

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