Potassium Carbonate → 3-[5-(6-Chloropurin-9-yl)pentyloxy]benzamide

HRID 429166Notes

Reaction equation

HRID 429166 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11]([NH2:13])=[O:12].[Cl:17][C:18]1[N:26]=[CH:25][N:24]=[C:23]2[C:19]=1[NH:20][CH:21]=[N:22]2.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:17][C:18]1[N:26]=[CH:25][N:24]=[C:23]2[C:19]=1[N:20]=[CH:21][N:22]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11]([NH2:13])=[O:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 53592776-ChloropurineHCID 183546093-(Bromopentyloxy)benzamide

Product 1

HCID 183546243-[5-(6-Chloropurin-9-yl)pentyloxy]benzamideYield 20%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-(bromopentyloxy)benzamide (500 mg, 1.7 mmols), 6-chloropurine (270 mg, 1.7 mmols) and potassium carbonate (240 mg, 1.7 mmols) in DMF (7.5 ml) was stirred for two days at room temperature. The solvent was then removed under vacuum (0.001 mmHg) and the white solid (mixture of N7 and N9 isomers) was chromatographed (silica, 10% MeOH/CH2CI2) to give a single product (N9 isomer) as a glass. This was triturated with ether (=5 ml) to give a white solid which was recrystallised from ethyl acetate to give the product (120 mg, 0.33 mmols, 20% yield)

Workup

  1. customThe solvent was then removed under vacuum (0.001 mmHg)
  2. additionthe white solid (mixture of N7 and N9 isomers)
  3. customwas chromatographed (silica, 10% MeOH/CH2CI2)
  4. customto give a single product (N9 isomer) as a glass
  5. customThis was triturated with ether (=5 ml)
  6. customto give a white solid which
  7. customwas recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-15a0c93450dd4202869c724eba9dcd1b
Source dataset
uspto-grants-2001_11
Patent number
US06316455B1

Reaction notes

Loading…