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

HRID 264725

Reaction equation

HRID 264725 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-4149bba3d5b6447a9a7cecd10150e7f6
Source dataset
uspto-grants-1997_07
Patent number
US05646265

Linked notes

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