Phenylacetyl chloride → HCID 178420877, compound

HRID 2081793Notes

Reaction equation

HRID 2081793 reaction equation
C1(CN[C:6]2[N:14]=[CH:13][N:12]=[C:11]3[C:7]=2[N:8]=[CH:9][N:10]3[C@H]2CC[C@@H](CO)O2)CC1.C(N(CC)CC)C.C1(CC(Cl)=O)C=CC=CC=1>C(#N)C.CN(C)C1C=CN=CC=1>[N:14]1[CH:6]=[C:7]2[C:11]([NH:10][CH:9]=[N:8]2)=[N:12][CH:13]=1

Participants

6

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 18649770HCID 18649770, compound

Product 1

HCID 178420877HCID 178420877, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

6-(Cyclopropylmethylamino)-9-[(2R,5S)-tetrahydro-5-(hydroxymethyl)-2-furyl]-9H-purine (0.5 g, 1.44 mmoles) was dissolved in 20 mL acetonitrile. 4-Dimethylaminopyridine (10.2 mg, 0.08 mmoles) and triethylamine (620 μL, 4.4 mmoles) were added and the flask was chilled in an ice bath under a nitrogen atmosphere. Phenylacetyl chloride (1.11 g, 7.2 mmoles, Aldrich Chemical Co., Madison, WI) was added dropwise to the flask over a period of 15 minutes. The reaction was stirred at room temperature for 0.5 hours. The reaction was quenched with methanol and solvents were removed under vacuo. The residue was dissolved in 2 mL CHCL3 /CH3OH (9:1) and chromatographed on a column of silica gel (5×15 cm) in the application solvent. Additional chromatography was performed on the product containing fractions using a Chromatotron 2 mm silica gel plate developed with a hexane:acetone mixture (7:3). Lyophilization of the product containing fractions afforded 0.459 g of 6 -(cyclopropylmethylamino)-9-[(2R,5S)-tetrahydro-5-[(phenylacetyl)methyl]-2-furyl)]-9H-purine as an oil (78% yield): m.p. <25° C.

Workup

  1. temperaturethe flask was chilled in an ice bath under a nitrogen atmosphere
  2. customThe reaction was quenched with methanol and solvents
  3. customwere removed under vacuo
  4. dissolutionThe residue was dissolved in 2 mL CHCL3 /CH3OH (9:1)
  5. customchromatographed on a column of silica gel (5×15 cm) in the application solvent
  6. additioncontaining fractions
  7. additionLyophilization of the product containing fractions

Sources & evidence

ORD record
ord-b0a1a9974fef4a30bb7953994f3a17b1
Source dataset
uspto-grants-1993_02
Patent number
US05185437

Reaction notes

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