Isopropanol → 1-beta-L-Ribofuranosyl-6-methyluracil

HRID 366951Notes

Reaction equation

HRID 366951 reaction equation
C([O:9][C@H:10]1[C@@H:14]([O:15]C(=O)C2C=CC=CC=2)[C@H:13]([CH2:24][O:25]C(=O)C2C=CC=CC=2)[O:12][C@@H:11]1[N:34]1[C:41]([CH3:42])=[CH:40][C:38](=[O:39])[NH:37][C:35]1=[O:36])(=O)C1C=CC=CC=1.CC(O)C>N>[C@H:11]1([N:34]2[C:41]([CH3:42])=[CH:40][C:38](=[O:39])[NH:37][C:35]2=[O:36])[O:12][C@@H:13]([CH2:24][OH:25])[C@H:14]([OH:15])[C@@H:10]1[OH:9]

Participants

4

Reactant 2

HCID 3776IsopropanolHCID 120432031-(2',3',5'-Tri-O-benzoyl-beta-L-ribofuranosyl)-6-methyluracil

Product 1

HCID 543042731-beta-L-Ribofuranosyl-6-methyluracil

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

A solution of 40 (4.50 g, 7.86 mmol) was dissolved in sat. methanolic ammonia (60 mL). The reaction mixture was heated at 100° C. for 17 h in a steel bomb. The reaction vessel was cooled to room temperature and concentrated to yield an oil. The reside was further purified by silica gel flash column chromatography using dichloromethane and methanol (9:1) as the eluent. Pure fractions were collected and evaporated to give a white solid. This was further recyrstallized from 2-propanol to afford 1.98 g (94%) of pure 41: mp 175-177° C.; 1H NMR (Me2SO-d6) δ 2.24 (s, 3H, CH3), 3.42-3.57 (m, 2H, C5'H), 3.68 (m, 1H, C4'H), 4.0 (m, 1H, C3'H), 4.53 (m, 1H, C2'H), 4.68, 4.94, 5.22 (m, 3H, 3 OH, D2O exchangeable), 5.43 (d, 1H, C1'H, J1', 2' =3.85 Hz), 5.56 (s, 1H, C5H) and 11.25 (s, 1H, NH). Anal. Calc. for C10H14N2O6 (258.23): C, 46.51; H, 5.46; N, 10.85. Found: C, 46.66; H, 5.26; N, 10.66.

Workup

  1. concentrationconcentrated
  2. customto yield an oil
  3. customThe reside was further purified by silica gel flash column chromatography
  4. customPure fractions were collected
  5. customevaporated
  6. customto give a white solid
  7. customto afford 1.98 g (94%) of pure 41

Sources & evidence

ORD record
ord-6b7327d5e5d44872a97dd8c20ccae581
Source dataset
uspto-grants-2000_10
Patent number
US06130326

Reaction notes

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