Cesium carbonate → HCID 86631157, compound

HRID 2235004Notes

Reaction equation

HRID 2235004 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[NH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C@@H:12]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].Cl[C:29]1[N:34]=[C:33]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:32]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[CH:31][N:30]=1>CN(C)C=O>[C:24]([O:23][C:21]([NH:20][C@H:12]([CH2:11][CH2:10][CH2:9][CH2:8][NH:7][C:29]1[N:34]=[C:33]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:32]([C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)=[CH:31][N:30]=1)[CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:22])([CH3:26])([CH3:25])[CH3:27]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 126742762-Chloro-4,5-diphenylpyrimidineHCID 86631158HCID 86631158, compound

Product 1

HCID 86631157HCID 86631157, compoundYield 5.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

481 mg (1.48 mmol) of cesium carbonate were added to a solution of 135 mg (0.49 mmol) of ethyl (R)-8-amino-4-tert-butoxycarbonylaminooctanoate in 3.5 ml of dimethylformamide, and the mixture was stirred at room temperature. After 60 minutes, a solution of 87 mg (0.33 mmol) of 2-chloro-4,5-diphenylpyrimidine in 2.5 ml of dimethylformamide was added, and the mixture was stirred at 90° C. for 6 hours. The solvent was concentrated and the residue was partitioned between ethyl acetate and water. The organic phase was dried and concentrated under high vacuum. The residue was purified by a preparative HPLC (Purosphere, gradient acetonitrile/(water+0.5% TFA), gradient 20% acetonitrile to 100% in 30 minutes). 10 mg of ethyl (R)-4-tert-butoxycarbonylamino-8-(4,5-diphenylpyrimidin-2-ylamino)octanoate were obtained. The product obtained in this way was stirred with 50% trifluoroacetic acid for 2 hours, mixed with water and freeze dried. 12 mg (4%) of the desired product were obtained.

Workup

  1. stirringthe mixture was stirred at 90° C. for 6 hours
  2. concentrationThe solvent was concentrated
  3. customthe residue was partitioned between ethyl acetate and water
  4. customThe organic phase was dried
  5. concentrationconcentrated under high vacuum
  6. customThe residue was purified by a preparative HPLC (Purosphere, gradient acetonitrile/(water+0.5% TFA), gradient 20% acetonitrile to 100% in 30 minutes)

Sources & evidence

ORD record
ord-f989f634852248689fe2c2be810e197b
Source dataset
uspto-grants-2010_05
Patent number
US07713988B2

Reaction notes

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