Diisopropylethylamine → HCID 18336811, compound

HRID 2297654Notes

Reaction equation

HRID 2297654 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[O:19][C:20]([CH2:23][CH3:24])=[CH:21][N:22]=2)[O:12]1.C(N(C(C)C)CC)(C)C.Cl.[NH2:35][CH:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1>C(O)(C)C>[CH2:23]([C:20]1[O: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:35][CH:36]3[CH2:41][CH2:40][O:39][CH2:38][CH2:37]3)[O:12]2)=[N:22][CH:21]=1)[CH3:24]

Participants

5

Reactant 3

HCID 81531Diisopropylethylamine2×HCID 441186934-Aminotetrahydropyran hydrochloride2×HCID 56627541HCID 56627541, compound

Product 1

HCID 18336811HCID 18336811, compoundYield 355.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of (2R,3R,4S,5S)-2-(6-chloro-purin-9-yl)-5-(5-ethyl-oxazol-2-yl)-tetrahydro-furan-3,4-diol (0.19 g), in isopropanol (15 ml) was added diisopropylethylamine (0.3 ml) and 4-aminotetrahydropyran hydrochloride (0.135 g). After stirring at reflux for 16 h, further diisopropylethylamine (0.2 ml) and 4-aminotetrahydropyran hydrochloride (60 mg) were added. Stirring was continued at reflux for a further 20 h before the mixture was cooled and concentrated in vacuo to give a yellow gum (0.8 g). Purification by chromatography on silica gel (Merck 7734) with dichloromethane:ethanol:ammonia (250:8:1)-(100:8:1), gave the title compound, as a white foam (0.182 g).

Workup

  1. temperatureat reflux for 16 h
  2. stirringStirring
  3. temperatureat reflux for a further 20 h before the mixture
  4. temperaturewas cooled
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-026e1398fac34e419e3205d201240400
Source dataset
uspto-grants-2002_12
Patent number
US06492348B1

Reaction notes

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