Allyl bromide → HCID 9994808, compound

HRID 1957492Notes

Reaction equation

HRID 1957492 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][C:7](=[O:16])[N:8]2[CH2:11][CH2:12][CH2:13][CH2:14][OH:15])=[C:4]([Cl:17])[N:3]=1.[H-].[Na+].[CH2:20](Br)[CH:21]=[CH2:22]>CN(C=O)C>[CH2:22]([N:6]1[C:5]2[C:9](=[N:10][C:2]([NH2:1])=[N:3][C:4]=2[Cl:17])[N:8]([CH2:11][CH2:12][CH2:13][CH2:14][OH:15])[C:7]1=[O:16])[CH:21]=[CH2:20]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 11777251HCID 11777251, compound

Product 1

HCID 9994808HCID 9994808, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-amino-6-chloro-9-(4-hydroxybutyl)-8-oxo-7H-purine (0.8 g, 3.1 mM) in DMF (15 mL) was added NaH (0.12 g, 60% oil dispersion, 3 mM) all at once at zero degrees C. under nitrogen and stirred for 30 minutes. To this was added allyl bromide (0.37 g, 3.1 mM) and the resulting mixture was allowed to warm to room temperature and stirred overnight. Most of solvent was removed in vacuo and the residue was purified by column chromatography on silica gel (120 g, CH2Cl2 /CH3OH/conc. NH4OH, 100/5/0.1) to give 7-allyl-2-amino-6-chloro-9-(4-hydroxybutyl)-8-oxo-7H-purine as an off-white powder (40 percent) mp 132°-133° C. IR (KBr) 3320, 1715, 1640, 1585, 1460 cm-1. 1H NMR (DMSO-d6) δ 6.70 (bs, 2H, exchangeable, NH2), 5.95 (m, 1H), 3.70 (t:, J=6.5 Hz, 2H, NCH2), 3.35 (m, 2H, CH2OH), 1.50 (m, 4H, CH2CH2).

Workup

  1. stirringstirred overnight
  2. customMost of solvent was removed in vacuo
  3. customthe residue was purified by column chromatography on silica gel (120 g, CH2Cl2 /CH3OH/conc. NH4OH, 100/5/0.1)

Sources & evidence

ORD record
ord-bd8bda93885643c6adcbb61624f01cba
Source dataset
uspto-grants-1998_07
Patent number
US05786359

Reaction notes

Loading…