Cesium carbonate → HCID 178472430, compound

HRID 2235002Notes

Reaction equation

HRID 2235002 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[NH2:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:10][CH2:9]1.Cl[C:20]1[N:25]=[C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:23]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:22][N:21]=1>C1(C)C=CC=CC=1>[C:26]1([C:24]2[C:23]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)=[CH:22][N:21]=[C:20]([NH:7][C@H:8]3[CH2:9][CH2:10][C@H:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:12][CH2:13]3)[N:25]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 126742762-Chloro-4,5-diphenylpyrimidineHCID 178472434HCID 178472434, compound

Product 1

HCID 178472430HCID 178472430, compoundYield 34.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

550 mg (1.69 mmol) of cesium carbonate were added to a suspension of 175 mg (0.84 mmol) of ethyl trans-4-aminocyclohexanecarboxylate in 5 ml of toluene, and the mixture was stirred at room temperature. After 30 minutes, 150 mg (0.56 mmol) of 2-chloro-4,5-diphenyl-pyrimidine were added, and the mixture was stirred at 120° C. for 4 days. The solvent was removed in vacuo and the residue was partitioned between dichloromethane and water. The organic phase was dried and concentrated under high vacuum. An attempt was made to purify the residue on a silica gel column (heptane/isopropanol, gradient 100% to 5% in 15 minutes). A mixed fraction was obtained, and the product crystallized therefrom. The precipitate was filtered off with suction. 78 mg (34%) of the desired product were obtained in this way.

Workup

  1. stirringthe mixture was stirred at 120° C. for 4 days
  2. customThe solvent was removed in vacuo
  3. customthe residue was partitioned between dichloromethane and water
  4. customThe organic phase was dried
  5. concentrationconcentrated under high vacuum
  6. customto purify the residue on a silica gel column (heptane/isopropanol, gradient 100% to 5% in 15 minutes)
  7. customA mixed fraction was obtained
  8. customthe product crystallized
  9. filtrationThe precipitate was filtered off with suction

Sources & evidence

ORD record
ord-2613b5b2a7c7468b87da617af70b00ce
Source dataset
uspto-grants-2010_05
Patent number
US07713988B2

Reaction notes

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