Triethylamine → HCID 56612472, compound

HRID 974263Notes

Reaction equation

HRID 974263 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:38])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]>CN(C)C1C=CN=CC=1.C(#N)C>[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][O:21][C:29](=[O:38])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[O:16]2)[CH2:2][CH2:3]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 69819Nonanoyl chlorideHCID 18649770HCID 18649770, compound

Product 1

HCID 56612472HCID 56612472, compoundYield 32.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

6-(Cyclopropylmethylamino)-9-[(2R,5S)-tetrahydro-5-(hydroxymethyl)-2-furyl]-9H-purine (0.498 g, 1.7 mmoles), 4-dimethylaminopyridine (10 mg, 0.1 mmoles, Aldrich Chemical Co., Madison, Wis.), and triethylamine (2.0 mL, 14 mmoles, Aldrich Chemical Co., Madison, Wis.) were dissolved in 50 mL acetonitrile. Nonanoyl chloride (1.26 mL, 7.0 mmoles, Aldrich Chemical Co., Madison, Wis.) was added and the reaction was stirred at room temperature for 3 hours. The reaction was quenched with methanol and solvents were evaporated in vacuo. The residue was dissolved in 25 mL ethyl acetate and undissolved salts were removed by filtration. After evaporation of the ethyl acetate, the residue was dissolved in methanol and passed over a silica gel column (4.8×13 cm). The product containing fractions were combined, concentrated, and chromatographed on a Chromatotron (4 mm silica gel plate) in a mixture of hexane:acetone (80:20). Two separate subsequent runs on the Chromatotron (4 mm silica gel plate) with a mixture of chloroform:acetone (95:5) and a mixture of hexane:acetone (85:15) followed by lyophilization afforded 0.236 g of 6-(cyclopropylmethylamino)-9-((2R,5S)-5-[(nonanoyloxy)methyl]-tetrahydro-2-furyl)-9H-purine as an oil (32% yield).

Workup

  1. customThe reaction was quenched with methanol and solvents
  2. customwere evaporated in vacuo
  3. dissolutionThe residue was dissolved in 25 mL ethyl acetate
  4. customundissolved salts were removed by filtration
  5. customAfter evaporation of the ethyl acetate
  6. dissolutionthe residue was dissolved in methanol
  7. additionThe product containing fractions
  8. concentrationconcentrated
  9. customchromatographed on a Chromatotron (4 mm silica gel plate) in a mixture of hexane:acetone (80:20)
  10. customTwo separate subsequent runs on the Chromatotron (4 mm silica gel plate)
  11. additionwith a mixture of chloroform:acetone (95:5)
  12. additiona mixture of hexane:acetone (85:15)

Sources & evidence

ORD record
ord-005c1b068c224ee1ba5e0bbc12fc6999
Source dataset
uspto-grants-1991_11
Patent number
US05068320

Reaction notes

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