Triethylamine → HCID 22854323, compound

HRID 1647178Notes

Reaction equation

HRID 1647178 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[NH2:3].[C:12]([O:20][C@@H:21]1[C@H:25]([O:26][C:27](=[O:34])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C@@H:24]([CH2:35][O:36][C:37](=[O:44])[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[O:23][C@H:22]1[N:45]1[CH:53]=[N:52][C:51]2[C:46]1=[N:47][C:48]([Cl:55])=[N:49][C:50]=2Cl)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C>O1CCOCC1>[C:12]([O:20][C@@H:21]1[C@H:25]([O:26][C:27](=[O:34])[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C@@H:24]([CH2:35][O:36][C:37](=[O:44])[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[O:23][C@H:22]1[N:45]1[C:46]2[N:47]=[C:48]([Cl:55])[N:49]=[C:50]([NH:3][N:2]([CH3:1])[CH2:4][CH2:5][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:51]=2[N:52]=[CH:53]1)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 116930649-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-2,6-dichloro-9H-purineHCID 19926386HCID 19926386, compound

Product 1

HCID 22854323HCID 22854323, compoundYield 163.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The above hydrochloride salt of 1-methyl-1-(2-phenylethyl)hydrazine (0.67 g, 1.05 mmol), 9-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (1.90 g, 3 mmol) and triethylamine (1.24 ml, 9 mmol) were dissolved in 1,4 -dioxan (20 ml). The solution was stirred at ambient temperature for 20 h. The cooled reaction mixture was evaporated to a gum and purified by flash chromatography on silica gel. Bution with cyclohexane/ethyl acetate (4/1) initially and then with a 1/1 mixture of these solvents provided 2',3',5'-tri-O-benzoyl-2-chloro-N-(N-methyl-N-(2-phenylethyl)amino)adenosine (1.28 g, 60%) as a foam, 1H NMR (DMSO-d6)γ 2.63 (3H, s,--CH3), 4.66 (1H, dd, H-5'a), 4.77 (1H, dd, H-5'b), 4.86 (1H, q, H-4'), 6.23 (1H, t, H-3'), 6.36 (1H, t, H-2'), 6.54 (1H, d, H-1'), 7.11-7.98 (20H, m, Ar-H), 8.44 (1H, s, H-8), 9.40 (1H, br s, N-H).

Workup

  1. customThe cooled reaction mixture
  2. customwas evaporated to a gum
  3. custompurified by flash chromatography on silica gel
  4. additionBution with cyclohexane/ethyl acetate (4/1) initially and then with a 1/1 mixture of these solvents

Sources & evidence

ORD record
ord-f401ca7fc3fa4123838932064efa077b
Source dataset
uspto-grants-1995_07
Patent number
US05430027

Reaction notes

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