Acetyl chloride → HCID 57228641, compound

HRID 974261Notes

Reaction equation

HRID 974261 reaction equation
[CH:1]1([CH2:4][NH:5][C:6]2[N:14]=[CH:13][N:12]=[C:11]3[C:7]=2[N:8]=[CH:9][N:10]3[C@H:15]2[CH2:19][CH2:18][C@@H:17]([CH2:20][OH:21])[O:16]2)[CH2:3][CH2:2]1.C(N(CC)CC)C.[C:29](Cl)(=[O:31])[CH3:30]>CN(C)C1C=CN=CC=1.C(#N)C>[C:29]([O:21][CH2:20][C@H:17]1[O:16][C@@H:15]([N:10]2[CH:9]=[N:8][C:7]3[C:11]2=[N:12][CH:13]=[N:14][C:6]=3[NH:5][CH2:4][CH:1]2[CH2:2][CH2:3]2)[CH2:19][CH2:18]1)(=[O:31])[CH3:30]

Participants

6

Reactant 3

HCID 6367Acetyl chloride2×HCID 8471Triethylamine2×HCID 18649770HCID 18649770, compound

Product 1

HCID 57228641HCID 57228641, compoundYield 52.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

6-(Cyclopropylmethylamino)-9-[(2R,5S)-tetrahydro-5-(hydroxymethyl)-2-furyl]-9H-purine (0.290 g, 1 mmoles), 4-dimethylaminopyridine (10.2 mg, 0.1 mmoles, Aldrich Chemical Co., Madison, Wis.), and triethylamine (620 μl, 4.4 mmoles, Aldrich Chemical Co., Madison, Wis.) were dissolved in 50 mL acetonitrile. The flask was chilled in an ice bath and acetyl chloride (150 μl, 2.1 mmoles, Aldrich Chemical Co., Madison, Wis.) was added. The reaction was brought to room temperature and stirred for 4 hours. Additional aliquots of triethylamine (620 μl, 4.4 mmoles) and acetyl chloride (150 μl, 2.1 mmoles) were added and the reaction was stirred overnight. The reaction was quenched with methanol and solvents were evaporated in vacuo. The residue was suspended in 25 mL ethyl acetate and salts were removed by filtration. Solvent was evaporated in vacuo and the remaining material was chromatographed on a Chromatotron (4 mm silica gel plate) with a mixture of hexane:acetone (7:3). Lyophilization afforded 0.174 g of 9-[(2R,5S)-5-(acetoxymethyl)-tetrahydro-2-furyl]-6-(cyclopropylmethylamino)-9H-purine as an oil (51% yield).

Workup

  1. temperatureThe flask was chilled in an ice bath
  2. customwas brought to room temperature
  3. stirringthe reaction was stirred overnight
  4. customThe reaction was quenched with methanol and solvents
  5. customwere evaporated in vacuo
  6. customsalts were removed by filtration
  7. customSolvent was evaporated in vacuo
  8. customthe remaining material was chromatographed on a Chromatotron (4 mm silica gel plate) with a mixture of hexane:acetone (7:3)

Sources & evidence

ORD record
ord-ac38c2b48c8b491c8e207d505458ddbd
Source dataset
uspto-grants-1991_11
Patent number
US05068320

Reaction notes

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