Ammonia → HCID 58078371, compound

HRID 722003Notes

Reaction equation

HRID 722003 reaction equation
C([O:4][CH2:5][C@@:6]1([CH3:28])[O:10][C@@H:9]([N:11]2[CH:19]=[C:17]([CH3:18])[C:15](=S)[NH:14][C:12]2=[O:13])[C@H:8]([O:20]C(=O)C)[C@@H:7]1[O:24]C(=O)C)(=O)C.[NH3:29]>>[CH3:28][C@:6]1([CH2:5][OH:4])[O:10][C@@H:9]([N:11]2[CH:19]=[C:17]([CH3:18])[C:15]([NH2:29])=[N:14][C:12]2=[O:13])[C@H:8]([OH:20])[C@@H:7]1[OH:24]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 86590643HCID 86590643, compound

Product 1

HCID 58078371HCID 58078371, compoundYield 57%

Procedure

Compound 16 (0.160 g, 0.386 mmol) was treated with methanolic ammonia (previously saturated at −10° C.), (10 mL) at 100° C. in a stainless-steel bomb for 3 hours, then cooled to room temperature. The solvent was evaporated under reduced pressure and the residue was partitioned between methylene chloride (30 mL) and water (30 mL). The aqueous layer was washed with methylene chloride (2×30 mL), concentrated under reduced pressure. The crude material was purified by silica gel column chromatography [eluent: 20% methanol in methylene chloride] to afford 1-(4-C-methyl-β-D-ribofuranosyl)-5-methyl-cytosine (60 mg, 57%). This compound was dissolved in EtOH 100 (1.5 mL), treated with a 2N hydrochloric acid solution (0.3 mL), and the mixture was stirred before being concentrated under reduced pressure. The procedure was repeated twice and 17 was precipitated from absolute ethanol. Mp: 194–200 (dec.); UV (H2O): λmax=275.6 nm (ε=7300), λmin=255 nm (ε=4700); HPLC 100%, 1H-NMR (DMSO-d6): δ 9.34 and 9.10 (2s, 2H, NH2), 8.21 (s, 1H, H-6), 5.80 (d, 1H, H-1′, J1′-2′=6.0 Hz), 5.3–4.3 (m, 3H, OH-2′, OH-3′ and OH-5′), 4.21 (t, 1H, H-2′, J=5.7 Hz), 3.98 (d, 1H, H-3′, J=5.3 Hz), 3.5–3.3 (m, 2H, H-5′ and H-5″), 1.97 (s, 3H, CH3), 1.12 (s, 3H, CH3).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was partitioned between methylene chloride (30 mL) and water (30 mL)
  3. washThe aqueous layer was washed with methylene chloride (2×30 mL)
  4. concentrationconcentrated under reduced pressure
  5. customThe crude material was purified by silica gel column chromatography [eluent: 20% methanol in methylene chloride]

Sources & evidence

ORD record
ord-e8a2c42c69b744209baf8445e82f5f16
Source dataset
uspto-grants-2006_11
Patent number
US07138376B2

Reaction notes

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