Sodium hydride → 4-Chloro-7-(3-chloro-1-phenyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 1869206Notes

Reaction equation

HRID 1869206 reaction equation
[Cl:1][C:2]1[C:3]2[CH:10]=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[H-].[Na+].[Cl:13][CH2:14][CH2:15][CH:16](OS(C)(=O)=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C=O)C.O.CCOC(C)=O>[Cl:1][C:2]1[C:3]2[CH:10]=[CH:9][N:8]([CH:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:15][CH2:14][Cl:13])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-HCID 57985877Methanesulfonic acid 3-chloro-1-phenyl-propyl ester

Product 1

HCID 579858984-Chloro-7-(3-chloro-1-phenyl-propyl)-7H-pyrrolo[2,3-d]pyrimidineYield 56%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a RT solution of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (424 mg, 2.76 mmol) in DMF (3 mL) was added NaH (60% in mineral oil, 121 mg, 3.03 mmol). The reaction mixture was stirred for 30 min at RT and then a solution of methanesulfonic acid 3-chloro-1-phenyl-propyl ester in DMF (2 mL) was added at 0° C. The resulting mixture was stirred overnight at RT and then diluted with H2O and EtOAc. The organic layer was separated, washed 3 times with water, dried over MgSO4, filtered, concentrated, and purified via flash chromatography (hexane/EtOAc), affording 4-Chloro-7-(3-chloro-1-phenyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine as a colorless oil (480 mg, 56% yield).

Workup

  1. stirringThe resulting mixture was stirred overnight at RT
  2. customThe organic layer was separated
  3. washwashed 3 times with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified via flash chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-ec0d0146a9154c9ba4cdb23782852c0e
Source dataset
uspto-grants-2009_12
Patent number
US07638517B2

Reaction notes

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