Cesium carbonate → HCID 73554645, compound

HRID 916776Notes

Reaction equation

HRID 916776 reaction equation
Br[CH2:2][CH:3]1[CH2:5][CH2:4]1.[Cl:6][C:7]1[C:8]2[CH:15]=[CH:14][NH:13][C:9]=2[N:10]=[CH:11][N:12]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Cl:6][C:7]1[C:8]2[CH:15]=[CH:14][N:13]([CH2:2][CH:3]3[CH2:5][CH2:4]3)[C:9]=2[N:10]=[CH:11][N:12]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 81503BromomethylcyclopropaneHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-

Product 1

HCID 73554645HCID 73554645, compoundYield 95.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(Bromomethyl)cyclopropane (7.6 mL, 78 mmol) was added to a solution of 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine (10.0 g, 65 mmol) and cesium carbonate (25.4 g, 78 mmol) in DMF (100 mL). The reaction mixture was stirred at room temperature 12 h, filtered, and concentrated in vacuo. Purification by flash column chromatography (silica, 1:9→2:8 EtOAc:hexanes) provided the title compound as a white solid (12.9 g, 95%). MS: 208.5 (MH+); HPLC Rf: 5.21 min. (HPLC method 4); HPLC purity: 100%.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customPurification by flash column chromatography (silica, 1:9→2:8 EtOAc:hexanes)

Sources & evidence

ORD record
ord-86de979844fb447f9284ead8c44a42df
Source dataset
uspto-grants-2007_09
Patent number
US07271262B2

Reaction notes

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