Sodium hydride → HCID 90402755, compound

HRID 2200701Notes

Reaction equation

HRID 2200701 reaction equation
[CH:1]1([O:7][CH2:8][CH2:9][OH:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Br[C:14]1[N:22]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)[C:21]2[C:20](=[O:31])[N:19]([CH2:32][CH2:33][CH2:34][O:35][CH:36]3[CH2:41][CH2:40][CH2:39][CH2:38][O:37]3)[C:18](=[O:42])[N:17]([CH3:43])[C:16]=2[N:15]=1>C1COCC1>[Cl:30][C:27]1[CH:26]=[CH:25][C:24]([CH2:23][N:22]2[C:21]3[C:20](=[O:31])[N:19]([CH2:32][CH2:33][CH2:34][O:35][CH:36]4[CH2:41][CH2:40][CH2:39][CH2:38][O:37]4)[C:18](=[O:42])[N:17]([CH3:43])[C:16]=3[N:15]=[C:14]2[O:10][CH2:9][CH2:8][O:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2247752-(Cyclohexyloxy)ethanol2×HCID 904026828-bromo-7-(4-chlorobenzyl)-3-methyl-1-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-1H-purine-2,6(3H,7H)-dione2×

Product 1

HCID 90402755HCID 90402755, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-(cyclohexyloxy)ethanol (63.4 mg, 0.439 mmol, intermediate 38) in THF (5 mL) was added sodium hydride (23.4 mg, 0.586 mmol, 60% dispersion in mineral oil) at 0° C., and the mixture was stirred at room temperature for 30 min. Then a solution of 8-bromo-7-(4-chlorobenzyl)-3-methyl-1-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-1H-purine-2,6(3H,7H)-dione (150 mg, 0.293 mmol, intermediate 14) in THF (1 mL) was added and the resulting mixture was stirred at reflux for 1 h. The reaction was cooled and quenched with ice-water. The mixture was extracted with ethyl acetate. The organic phase was dried and concentrated to give 7-(4-chlorobenzyl)-8-(2-(cyclohexyloxy)ethoxy)-3-methyl-1-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-1H-purine-2,6(3H,7H)-dione (123 mg, 73% yield) as a yellow solid. LCMS retention time 2.064 min; LCMS MH+-THP 491.

Workup

  1. stirringthe resulting mixture was stirred
  2. temperatureat reflux for 1 h
  3. temperatureThe reaction was cooled
  4. customquenched with ice-water
  5. extractionThe mixture was extracted with ethyl acetate
  6. customThe organic phase was dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ffc93b17010847d685b697600a073490
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

Loading…