HCID 15277404, compound → HCID 86607299, compound

HRID 552753Notes

Reaction equation

HRID 552753 reaction equation
C([O:4][C@H:5]1[C@@H:9]2[O:10][Si:11]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[O:12][Si:13]([CH:19]([CH3:21])[CH3:20])([CH:16]([CH3:18])[CH3:17])[O:14][CH2:15][C@H:8]2[O:7][C@H:6]1[N:28]1[CH:36]=[N:35][C:34]2[C:29]1=[N:30][CH:31]=[N:32][C:33]=2[Cl:37])(=O)C>N.CO>[Cl:37][C:33]1[N:32]=[CH:31][N:30]=[C:29]2[C:34]=1[N:35]=[CH:36][N:28]2[C@@H:6]1[O:7][C@H:8]2[C@@H:9]([O:10][Si:11]([CH:22]([CH3:24])[CH3:23])([CH:25]([CH3:27])[CH3:26])[O:12][Si:13]([CH:19]([CH3:20])[CH3:21])([CH:16]([CH3:17])[CH3:18])[O:14][CH2:15]2)[C@@H:5]1[OH:4]

Participants

4

Reactant 1

HCID 15277404HCID 15277404, compound

Product 1

HCID 86607299HCID 86607299, compoundYield 94.2%

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

(6aR,8R,9S,9aR)-8-(6-chloro-9H-purin-9-yl)-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-9-yl acetate (3.51 g, 6.14 mmol) (Kittaka, A.; Yamada, N.; Tanaka, H.; Nakamura, K. T.; Miyasaka, T. Nucleosides Nucleotides, 1996, 15, 1447-1457) was stirred in 7N NH3 in MeOH (2.33 mL) for 2.5 h. The mixture was then concentrated and the residue was purified by flash chromatography (20 to 50% EtOAc/hexanes) to give title compound as a light yellow foam (3.06 g, 92%).

Workup

  1. concentrationThe mixture was then concentrated
  2. customthe residue was purified by flash chromatography (20 to 50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-5929ae2aa2894ee8835d56037fe4a4bd
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

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