Ammonium Chloride → 4-phenethyl-7H-pyrrolo[2,3-d]pyrimidine

HRID 552775Notes

Reaction equation

HRID 552775 reaction equation
[CH2:1]([Mg]Br)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:12]1[C:13]2[CH:20]=[CH:19][NH:18][C:14]=2[N:15]=[CH:16][N:17]=1.[NH4+].[Cl-]>C1COCC1>[C:3]1([CH2:2][CH2:1][C:12]2[C:13]3[CH:20]=[CH:19][NH:18][C:14]=3[N:15]=[CH:16][N:17]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-HCID 178419670HCID 178419670, compound

Product 1

HCID 671649194-phenethyl-7H-pyrrolo[2,3-d]pyrimidineYield 54.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Phenethyl magnesium bromide (0.5 M solution in THF, 12 mL, 6.15 mmol) was added dropwise to a stirred solution of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (0.210 g, 1.37 mmol) and Fe(acac)3 (0.1 g 0.273 mmol) in THF (5.0 mL) under Ar. The resulting reaction mixture was stirred at r.t. for 8 h. The mixture was poured onto a mixture of ice (10 mL) and NH4Cl (0.5 g) and the product was extracted with CHCl3. The combined organics were dried (Na2SO4), filtered and concentrated. The crude product was purified by flash chromatography (0 to 10% MeOH/DCM) to afford the title compound (0.166 g, 54%).

Workup

  1. customThe resulting reaction mixture
  2. extractionthe product was extracted with CHCl3
  3. dry with materialThe combined organics were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography (0 to 10% MeOH/DCM)

Sources & evidence

ORD record
ord-cb1130a9fd9c4e1284fc08e6916e4e7e
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

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