Sodium hydride → HCID 90402773, compound

HRID 2200551Notes

Reaction equation

HRID 2200551 reaction equation
[F:1][C:2]([F:15])([F:14])[O:3][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)[O:7][CH2:8][CH2:9][OH:10].[H-].[Na+].Br[C:19]1[N:27]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[C:26]2[C:25](=[O:36])[N:24]([CH2:37][CH2:38][CH2:39][O:40][CH:41]3[CH2:46][CH2:45][CH2:44][CH2:43][O:42]3)[C:23](=[O:47])[N:22]([CH3:48])[C:21]=2[N:20]=1>C1COCC1>[CH3:48][N:22]1[C:21]2[N:20]=[C:19]([O:10][CH2:9][CH2:8][O:7][C:6]3[CH:11]=[CH:12][CH:13]=[C:4]([O:3][C:2]([F:14])([F:15])[F:1])[CH:5]=3)[N:27]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:33])[CH3:34])[C:26]=2[C:25](=[O:36])[N:24]([CH2:37][CH2:38][CH2:39][O:40][CH:41]2[CH2:46][CH2:45][CH2:44][CH2:43][O:42]2)[C:23]1=[O:47]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 22036406HCID 22036406, compound2×HCID 90402652HCID 90402652, compound2×

Product 1

HCID 90402773HCID 90402773, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(3-(trifluoromethoxy)phenoxy)ethanol (0.64 g, 2.9 mmol, intermediate 5) in THF (15 mL) was added sodium hydride (0.23 g, 9.67 mmol) at 0° C. it was stirred at 0° C. for 30 min, then 8-bromo-3-methyl-1-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-1H-purine-2,6(3H,7H)-dione (1.0 g, 1.93 mmol, intermediate 16 step 1) was added. The mixture was stirred 16 h. The reaction was quenched with aq. ammonium chloride (2 mL) at 0° C.; then it was partitioned between ethyl acetate and water. The organic phases were combined, dried over sodium sulfate, filtered and concentrated to give a crude product which was used without purification. LCMS retention time 2.144; LCMS MH+-THP 575.

Workup

  1. stirringThe mixture was stirred 16 h
  2. customThe reaction was quenched with aq. ammonium chloride (2 mL) at 0° C.
  3. customthen it was partitioned between ethyl acetate and water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4ab2c9824da6458cb9c2a5ec9a14c016
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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