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

HRID 722757Notes

Reaction equation

HRID 722757 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 appropriate fractions 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. customThe appropriate fractions were evaporated

Sources & evidence

ORD record
ord-423d14d6d27f4857ab52308e229dfc6d
Source dataset
uspto-grants-2006_11
Patent number
US07138517B2

Reaction notes

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