1-Chloro-4-(chloromethyl)benzene → HCID 59834740, compound

HRID 271610Notes

Reaction equation

HRID 271610 reaction equation
[CH3:1][C:2]([CH3:24])([CH3:23])[CH2:3][N:4]1[C:8]2[N:9]=[C:10]([C:13]#[N:14])[N:11]=[CH:12][C:7]=2[CH:6]=[C:5]1[CH2:15][N:16]1[C:20](=[O:21])[CH2:19][NH:18][C:17]1=[O:22].C([O-])([O-])=O.[K+].[K+].[Cl:31][C:32]1[CH:39]=[CH:38][C:35]([CH2:36]Cl)=[CH:34][CH:33]=1>CN(C=O)C>[Cl:31][C:32]1[CH:39]=[CH:38][C:35]([CH2:36][N:18]2[CH2:19][C:20](=[O:21])[N:16]([CH2:15][C:5]3[N:4]([CH2:3][C:2]([CH3:24])([CH3:23])[CH3:1])[C:8]4[N:9]=[C:10]([C:13]#[N:14])[N:11]=[CH:12][C:7]=4[CH:6]=3)[C:17]2=[O:22])=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 11430Potassium CarbonateHCID 59834741HCID 59834741, compound

Product 1

HCID 59834740HCID 59834740, compoundYield 73.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 200 mg (0.61 mmoles) of 7-(2,2-dimethyl-propyl)-6-(2,5-dioxo-imidazolidin-1-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile in 10 ml of DMF, 136 mg (0.98 mmoles) of K2CO3, 138 mg (0.86 mmoles) of p-chlorobenzylchloride in 2 ml of DMF and 142 mg (0.86 mmoles) of KI are added successively at ambient temperature. After being stirred for 18 hours, the reaction mixture is quenched with ice water and extracted with AcOEt. The combined extracts are washed with H2O, brine and dried over MgSO4. Chromatography on silica gel (eluent: CH2C2:AcOEt=8:1) give 203 mg of desired 6-[3-(4-chloro-benzyl)-2,5-dioxo-imidazolidin-1-ylmethyl]-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile in 73% yield.

Workup

  1. customthe reaction mixture is quenched with ice water
  2. extractionextracted with AcOEt
  3. washThe combined extracts are washed with H2O, brine
  4. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-72da5e96c87d494fb8e799a9ae4d2d4c
Source dataset
uspto-grants-2008_11
Patent number
US07452886B2

Reaction notes

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