Ammonia → HCID 53967906, compound

HRID 1438831Notes

Reaction equation

HRID 1438831 reaction equation
[C:1]([CH2:3][C:4]1[N:8]([C@@H:9]2[O:21][C@H:20]([CH3:22])[C@@H:15]([O:16]C(=O)C)[C@H:10]2[O:11]C(=O)C)[CH:7]=[N:6][C:5]=1[C:23]([O:25]C)=O)#[N:2].[NH3:27]>>[C:1]([CH2:3][C:4]1[N:8]([C@@H:9]2[O:21][C@H:20]([CH3:22])[C@@H:15]([OH:16])[C@H:10]2[OH:11])[CH:7]=[N:6][C:5]=1[C:23]([NH2:27])=[O:25])#[N:2]

Participants

3

Reactant 2

HCID 222Ammonia2×HCID 53754841HCID 53754841, compound

Product 1

HCID 53967906HCID 53967906, compound

Procedure

A mixture of methyl 5-cyanomethyl-1-(5-deoxy-2,3-di-O-acetyl-β-D-ribofuranosyl)imidazole-4-carboxylate (2.20 g, 6.03 mmol) and liquid ammonia (30 ml) was placed in a steel bomb (40 ml) and heated at 100° for 7 hr. The ammonia was allowed to evaporate and the residue was subjected to a vacuum overnight to remove the last traces. The residue was absorbed on silica gel (5 g) and placed on a column of silica gel (60 g, packed in chloroform). Elution with chloroform-methanol (4:1) provided the pure product. Recrystallization from methanol provided colorless cubes (1.42 g, 88%); mp 173°-174° after drying at 100° for 3 hr; [α]D25 -47.8 C=1, H2O); uv λmaxpH 1 218 nm (ε 10,000), λmaxpH 7 233 nm (ε 10,200), λmaxpH 11 234 nm (ε 9,730); pmr (DMSO-d6): δ 1.35 (d,3,CH3), 5.66 (d,1,H1'), J = 5 Hz, 7.45 (d,2,NH2), 8.02 (s,1,C2H).

Workup

  1. temperatureheated at 100° for 7 hr
  2. customto evaporate
  3. customwas subjected to a vacuum overnight
  4. customto remove the last traces
  5. customThe residue was absorbed on silica gel (5 g)
  6. washElution with chloroform-methanol (4:1)
  7. customprovided the pure product
  8. customRecrystallization from methanol provided colorless cubes (1.42 g, 88%)
  9. custommp 173°-174° after drying at 100° for 3 hr

Sources & evidence

ORD record
ord-137f0dc06d9943dcbeb378e428a19dc4
Source dataset
uspto-grants-1977_11
Patent number
US04056674

Reaction notes

Loading…