Cesium carbonate → HCID 67416103, compound

HRID 1423003Notes

Reaction equation

HRID 1423003 reaction equation
[Cl:1][C:2]1[NH:3][CH:4]=[C:5]2[C:10]=1[C:9](=[O:11])[N:8]([CH3:12])[C:7](=[O:13])[N:6]2[CH2:14][CH:15]([CH3:17])[CH3:16].Cl[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=2)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C([O-])(O)=O.[Na+]>[Cl:1][C:2]1[N:3]([CH2:19][C:20]2[CH:21]=[CH:22][C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=3)=[CH:24][CH:25]=2)[CH:4]=[C:5]2[C:10]=1[C:9](=[O:11])[N:8]([CH3:12])[C:7](=[O:13])[N:6]2[CH2:14][CH:15]([CH3:17])[CH3:16]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 219897292-(4-(Chloromethyl)phenyl)pyridineHCID 67415912HCID 67415912, compound

Product 1

HCID 67416103HCID 67416103, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A suspension of crude 5-chloro-1-isobutyl-3-methyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (0.032 mmol), 2-(4-(chloromethyl)phenyl)pyridine (9.7 mg, 0.048 mmol) and cesium carbonate (15.6 mg, 0.048 mmol) in anhydrous DMF is stirred at room temperature for 3 h, and then diluted with saturated NaHCO3 aqueous solution, followed by extractions with CH2Cl2. The combined organic phase is dried over sodium sulfate, filtered, and concentrated to dryness under reduced pressure to give crude product, which is used in the next step without further purification. MS (ESI) m/z 423.1 [M+H]+.

Workup

  1. extractionfollowed by extractions with CH2Cl2
  2. dry with materialThe combined organic phase is dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to dryness under reduced pressure
  5. customto give crude product, which
  6. customis used in the next step without further purification

Sources & evidence

ORD record
ord-166ff67ab6c842259fdfe26d079ad3ea
Source dataset
uspto-grants-2015_01
Patent number
US08927556B2

Reaction notes

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