1-Iodooctadecane → 2,6-Diamino-9-(2-O-octadecyl-beta-D-ribofuranosyl)purine

HRID 2212484Notes

Reaction equation

HRID 2212484 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@H:12]2[OH:13])=[C:4]([NH2:20])[N:3]=1.[H-].[Na+].I[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]>CN(C=O)C>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@H:12]2[O:13][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH3:24])=[C:4]([NH2:20])[N:3]=1

Participants

5

Reactant 3

HCID 124021-IodooctadecaneHCID 24758Sodium hydrideHCID 722002-Aminoadenosine

Product 1

HCID 117311872,6-Diamino-9-(2-O-octadecyl-beta-D-ribofuranosyl)purineYield 11.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,6-Diamino-9-(β-D-ribofuranosyl)purine (50 g, 180 mmol) and sodium hydride (7 g) in DMF (1 l) were heated to boiling for 2 hr. Iodooctadecane (100 g) was added at 150° C. and the reaction mixture allowed to cool to RT. The reaction mixture was stirred for 11 days at RT. The solvent was evaporated and the residue purified by silica gel chromatography. The product was eluted with 5% MeOH/CH2Cl2. The product containing fraction were evaporated to yield the product (11 g). 1H NMR (DMSO-d6) δ 0.84 (t, 3, CH2); 1.22 [m, 32, O—CH2—CH2—(CH2)16—]; 1.86 (m, 2, O—CH2CH2—); 3.25 (m, 2, O—CH2—); 3.93 (d, 1, 4′H), 4.25 (m, 1, 3′H); 4.38 (t, 1, 2′H); 5.08 (d, 1, 3′-OH); 5.48 (t, 1, 5′-OH); 5.75 (s, 2, 6-NH2); 5.84 (d, 1, 1′-H); 6.8 (s, 2, 2-NH2); and 7.95 (s, 1, 8-H).

Workup

  1. customThe solvent was evaporated
  2. customthe residue purified by silica gel chromatography
  3. washThe product was eluted with 5% MeOH/CH2Cl2
  4. additionThe product containing fraction
  5. customwere evaporated

Sources & evidence

ORD record
ord-76e6c7b881654dc1a0f9097db513d783
Source dataset
uspto-grants-2006_09
Patent number
US07101993B1

Reaction notes

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