Diisopropylethylamine → HCID 18336813, compound

HRID 1839236Notes

Reaction equation

HRID 1839236 reaction equation
[C:1]([C:5]1[O:9][C:8]([C@@H:10]2[C@@H:14]([OH:15])[C@@H:13]([OH:16])[C@H:12]([N:17]3[CH:25]=[N:24][C:23]4[C:18]3=[N:19][CH:20]=[N:21][C:22]=4Cl)[O:11]2)=[N:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:28][CH:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1.C(N(C(C)C)CC)(C)C>C(O)(C)C>[C:1]([C:5]1[O:9][C:8]([C@@H:10]2[C@@H:14]([OH:15])[C@@H:13]([OH:16])[C@H:12]([N:17]3[CH:25]=[N:24][C:23]4[C:18]3=[N:19][CH:20]=[N:21][C:22]=4[NH:28][CH:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)[O:11]2)=[N:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 10156645HCID 10156645, compoundHCID 441186934-Aminotetrahydropyran hydrochloride

Product 1

HCID 18336813HCID 18336813, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

(2S,3S,4R,5R)-2-(5-tert-Butyl-[1,3,4]oxadiazol-2-yl)-5-(6-chloro-purin-9-yl)-tetrahydro-furan-3,4-diol (41 mg) was heated under reflux with 4-aminotetrahydropyran hydrochloride (59 mg), diisopropylethylamine (0.11 ml), and isopropanol (5 ml) for 15 h. The solvent was evaporated in vacuo and the residue purified by chromatography on silica gel, eluting with ethyl acetate:methanol 100:0-90:10, to give the title compound (37 mg).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue purified by chromatography on silica gel
  3. washeluting with ethyl acetate:methanol 100:0-90:10

Sources & evidence

ORD record
ord-8d5dccd92fdc400f95b25d9ddcfd1b56
Source dataset
uspto-grants-2004_01
Patent number
US06677316B2

Reaction notes

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