Sodium hydride → HCID 59841049, compound

HRID 874906Notes

Reaction equation

HRID 874906 reaction equation
[OH:1][CH:2]([C:4]1[N:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:12](=[O:20])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[CH3:21])[N:5]=1)[CH3:3].[H-].[Na+].Cl[C:25]1[N:33]=[CH:32][N:31]=[C:30]2[C:26]=1[N:27]=[CH:28][N:29]2[CH2:34][O:35][CH2:36][CH2:37][Si:38]([CH3:41])([CH3:40])[CH3:39]>C1COCC1>[CH3:21][C:10]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:11]=1[C:12](=[O:20])[N:13]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:4]([CH:2]([O:1][C:25]1[N:33]=[CH:32][N:31]=[C:30]3[C:26]=1[N:27]=[CH:28][N:29]3[CH2:34][O:35][CH2:36][CH2:37][Si:38]([CH3:41])([CH3:40])[CH3:39])[CH3:3])=[N:5]2

Participants

5

Reactant 3

HCID 24758Sodium hydride2×HCID 108698516-chloro-9-(2-trimethylsilanyl-ethoxymethyl)-9H-purine2×HCID 59841037HCID 59841037, compound

Product 1

HCID 59841049HCID 59841049, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of compound 181 (0.069 g, 0.25 mmol) in THF (5 mL) was treated with sodium hydride (0.007 g, 0.27 mmol) and stirred for 10 min. A solution of intermediate compound 13 (0.077 g, 0.27 mmol) in THF (1 mL) was added to the reaction mixture. The flask originally containing the intermediate compound 13 was washed with additional THF (1 mL) and the washings were also added to the reaction mixture. The reaction was allowed to proceed, and additional sodium hydride (0/005 g, 0.21 mmol) was added at 21.5 h and 23 h. The reaction was quenched after a total of 24 h by addition of saturated ammonium chloride solution (5 mL). The mixture was extracted with dichloromethane (3×5 mL), and the combined organic extracts were dried over MgSO4. After filtration, the filtrate was concentrated under reduced pressure and the residue was purified by flash chromatography (1:1 EtOAc:hexanes->3:2 EtOAc:hexanes) to give compound 182. ESI-MS m/z=529 (MH+). The reaction described above and compound 182 are shown below.

Workup

  1. washwas washed with additional THF (1 mL)
  2. additionthe washings were also added to the reaction mixture
  3. customThe reaction was quenched after a total of 24 h
  4. additionby addition of saturated ammonium chloride solution (5 mL)
  5. extractionThe mixture was extracted with dichloromethane (3×5 mL)
  6. dry with materialthe combined organic extracts were dried over MgSO4
  7. filtrationAfter filtration
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customthe residue was purified by flash chromatography (1:1 EtOAc:hexanes->3:2 EtOAc:hexanes)

Sources & evidence

ORD record
ord-57deee8cdee04d08a45f0c55a4e490e2
Source dataset
uspto-grants-2015_03
Patent number
US08980901B2

Reaction notes

Loading…