Diisopropylethylamine → HCID 18336826, compound

HRID 2297658Notes

Reaction equation

HRID 2297658 reaction equation
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@H:11]1[C@H:15]([OH:16])[C@H:14]([OH:17])[C@@H:13]([C:18]2[NH:19][N:20]=[CH:21][CH:22]=2)[O:12]1.C(N(CC)C(C)C)(C)C.Cl.[O:33]1[CH2:38][CH2:37][CH:36]([NH2:39])[CH2:35][CH2:34]1>C(O)(C)C>[N:20]1[NH:19][C:18]([C@@H:13]2[C@H:14]([OH:17])[C@H:15]([OH:16])[C@H:11]([N:6]3[CH:5]=[N:4][C:3]4[C:7]3=[N:8][CH:9]=[N:10][C:2]=4[NH:39][CH:36]3[CH2:37][CH2:38][O:33][CH2:34][CH2:35]3)[O:12]2)=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 441186934-Aminotetrahydropyran hydrochlorideHCID 86588178HCID 86588178, compound

Product 1

HCID 18336826HCID 18336826, compoundYield 12.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

(2R,3R,4S,5R)-2-(6-Chloro-purin-9-yl)-5-(2H-pyrazol-3-yl)-tetrahydro-furan-3,4-diol (35 mg) was dissolved in isopropanol (3 ml), N,N-di-isopropylethylamine (0.12 ml) and tetrahydro-pyran-4-ylamine hydrochloride (46 mg) were added, and the resulting solution was heated under reflux under nitrogen for 17 h. The solvent was removed in vacuo, the residue dissolved in methanol (10 ml), and 8% sodium bicarbonate (3 ml) added, followed by silica gel (3 g). The solvents were removed in vacuo and the residue added to a flash column of silica gel packed in dichloromethane. Elution with dichloromethane-methanol (4:1) afforded the title compound as a clear viscous gum (5.2 mg).

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureunder reflux under nitrogen for 17 h
  3. customThe solvent was removed in vacuo
  4. dissolutionthe residue dissolved in methanol (10 ml)
  5. addition8% sodium bicarbonate (3 ml) added
  6. customThe solvents were removed in vacuo
  7. additionthe residue added to a flash column of silica gel
  8. washElution with dichloromethane-methanol (4:1)

Sources & evidence

ORD record
ord-81156119ca9d47bb8da1ceb45382bf10
Source dataset
uspto-grants-2002_12
Patent number
US06492348B1

Reaction notes

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