Adenosine → HCID 136478604, compound

HRID 232531Notes

Reaction equation

HRID 232531 reaction equation
[C@H:1]1([N:9]2[CH:17]=[N:16][C:15]3[C:10]2=[N:11][C:12]([NH2:19])=[N:13][C:14]=3N)[S:6][C@H:5]([CH2:7][OH:8])[C@@H:3]([OH:4])[CH2:2]1.[C@@H]1(N2C3N=CN=C(N)C=3N=C2)O[C@H](CO)[C@@H](O)[C@H]1[OH:22]>O>[C@H:1]1([N:9]2[CH:17]=[N:16][C:15]3[C:14](=[O:22])[NH:13][C:12]([NH2:19])=[N:11][C:10]2=3)[S:6][C@H:5]([CH2:7][OH:8])[C@@H:3]([OH:4])[CH2:2]1

Participants

4

Reactant 2

HCID 60961AdenosineHCID 5271067HCID 5271067, compound2×

Product 1

HCID 136478604HCID 136478604, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 9-(2-deoxy-4-thio-α-D-ribofuranosyl)-2,6-diaminopurine (formula 8) (30 mg, 0.11 mmol) in distilled H2O (10 mL) was added a suspension of adenosine deaminase in 3.2M (NH4)2SO4 (0.1 mL) and reaction mixture was kept at room temperature. A 12-day TLC aliquot showed complete reaction. The solution was evaporated to dryness, the residue was crystallized from EtOH to give 9-(2-deoxy-4-thio-α-D-ribofuranosyl)-2-amino-1,6-dihydro-6-oxopurine (28 mg, 93%); mp 257°-260° C.; TLC 3: 1 CHCl3, MeOH, Rf 0.55; MS z/e 284 (M+1)+, UV λmax pH 1 254 (11.15), pH 7 254 (12.51), pH 13 267 (11.09); 1H NMR (Me2SO-d6, 300 MHz) δ2.30-2.40 (m, 1, H-2'), 2.52-2.62 (m, 1, H-2'), 3.30-3.40 (m, 1, H-5'), 3.46-3.58 (m, 1, H-5'), 3.60-3.66 (m, 1, H-4'), 4.46 (br t, 1, H-3'), 5.04 (br t, 1, 5'-OH), 5.50 (d, 1, 3'-OH, J=4 Hz), 5.94 (dd, 1, H-1', J=4 and 8 Hz), 6.50 (s, 2,NH2), 8.08 (s, 1, H-8); 13C NMR (Me2SO-d6, 300 MHz) δ42.57 (C-2'), 57.32 (C-1'), 59.63 (C-4'), 63.58 (C-5'), 74.34 (C-3'), 116.09 (C-5), 136.53 (C-8), 150.63 (C-4), 153.41 (C-2), 156.54 (C-6). Anal. (C10H13N5O3S) C, H, N, S.

Workup

  1. customreaction mixture
  2. customwas kept at room temperature
  3. customA 12-day TLC aliquot showed complete reaction
  4. customThe solution was evaporated to dryness
  5. customthe residue was crystallized from EtOH

Sources & evidence

ORD record
ord-561760fd13354158a918a901f940c374
Source dataset
uspto-grants-1997_01
Patent number
US05591722

Reaction notes

Loading…