Dimethyl Sulfoxide → 4-[5-{5H-Dibenzo[a,d]cyclohepten-5-yl}3,4-dihydro-2-oxo-4-thioxo-1(2H)-pyrimidinyl]benzoic acid, ethyl ester

HRID 1531932Notes

Reaction equation

HRID 1531932 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)[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-].[K+].[K+].F[C:31]1[CH:41]=[CH:40][C:34]([C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:33][CH:32]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C[S:49](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](=[S:49])[NH:18][C:19](=[O:22])[N:20]([C:31]4[CH:41]=[CH:40][C:34]([C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:33][CH:32]=4)[CH:21]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 5

HCID 679Dimethyl SulfoxideHCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 67976Benzoic acid, 4-fluoro-, ethyl esterHCID 110986755-(5h-Dibenzo[a,d]cyclohepten-5-yl)-2,4(1h,3h)-pyrimidinedione

Product 1

HCID 1317224374-[5-{5H-Dibenzo[a,d]cyclohepten-5-yl}3,4-dihydro-2-oxo-4-thioxo-1(2H)-pyrimidinyl]benzoic acid, ethyl ester

Conditions

Temperature
100 °C

Procedure

A mixture of the product of example 2 step (ii) (1.5 g), potassium carbonate (1.71 g) and ethyl 4-fluorobenzoate (0.835 g) in dimethylsulphoxide (20 ml ) was heated at 100° C. for 20 hours. Cesium carbonate(1.6 g) was added and the mixture heated at 100° C. for 5 hours. The mixture was partitioned between ethyl acetate and water. The organic phase was dried (MgSO4) and evaporated. Purified by chromatography 20-30% ethyl acetate in isohexane. Yield 0.72 g.

Workup

  1. temperaturethe mixture heated at 100° C. for 5 hours
  2. customThe mixture was partitioned between ethyl acetate and water
  3. dry with materialThe organic phase was dried (MgSO4)
  4. customevaporated
  5. customPurified by chromatography 20-30% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-364450bf971541bab435e960808421f0
Source dataset
uspto-grants-2001_03
Patent number
US06200981B1

Reaction notes

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