Ammonia → HCID 58781869, compound

HRID 1373685Notes

Reaction equation

HRID 1373685 reaction equation
N.C([O:5][C@@H:6]1[CH2:10][C@@H:9]([CH2:11][O:12]C(=O)C2C=CC=CC=2)[O:8][C@H:7]1[N:21]1[CH:29]=[N:28][C:27]2[C:22]1=[N:23][CH:24]=[N:25][C:26]=2[NH:30][CH:31]1[CH2:36][CH2:35][CH:34]([OH:37])[CH2:33][CH2:32]1)(=O)C.OC1CCC(NC2N=CN=C3C=2N=CN3[C@H]2[C@H](O)C[C@@H](COC(=O)C3C=CC=CC=3)O2)CC1>CO>[OH:37][CH:34]1[CH2:35][CH2:36][CH:31]([NH:30][C:26]2[N:25]=[CH:24][N:23]=[C:22]3[C:27]=2[N:28]=[CH:29][N:21]3[C@H:7]2[C@H:6]([OH:5])[CH2:10][C@@H:9]([CH2:11][OH:12])[O:8]2)[CH2:32][CH2:33]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 69426603HCID 69426603, compoundHCID 69428559HCID 69428559, compound

Product 1

HCID 58781869HCID 58781869, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methanol saturated with ammonia (20 mL) at 0° C. was added to a mixture of (5S,2R,3R)-2-{6-[(4-hydroxycyclohexyl)amino]purin-9-yl}-5-(benzoyloxymethyl)oxolan-3-yl acetate and (5S,2R,3R)-2-{6-[(4-hydroxycyclohexyl)amino]purin-9-yl}-5-(benzoyloxymethyl)oxolan-3-ol. The mixture was stirred at room temperature for 36 hours. The solvent was evaporated under reduced pressure, and the residue was purified on a Chromatotron to obtain (5S,2R,3R)-2-{6-[(4-hydroxycyclohexyl)amino]purin-9-yl}-5-(hydroxymethyl)oxolan-3-ol, a compound of Formula I.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified on a Chromatotron

Sources & evidence

ORD record
ord-a3c2e48d0c474299bac7fd459e95bd4e
Source dataset
uspto-grants-2007_01
Patent number
US07163928B2

Reaction notes

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