Water → HCID 18767628, compound

HRID 2105676Notes

Reaction equation

HRID 2105676 reaction equation
C([O:3][P:4]([CH2:9][CH2:10][C:11]12[CH2:18][CH2:17][C:14]([C:19]3[NH:27][C:26]4[C:25](=[O:28])[N:24]([CH2:29][CH2:30][CH3:31])[C:23](=[O:32])[N:22]([CH2:33][CH2:34][CH3:35])[C:21]=4[N:20]=3)([CH2:15][CH2:16]1)[CH2:13][CH2:12]2)(=[O:8])[O:5]CC)C.C[Si](Br)(C)C.O>C(Cl)Cl>[O:32]=[C:23]1[N:22]([CH2:33][CH2:34][CH3:35])[C:21]2[N:20]=[C:19]([C:14]34[CH2:15][CH2:16][C:11]([CH2:10][CH2:9][P:4](=[O:3])([OH:5])[OH:8])([CH2:12][CH2:13]3)[CH2:18][CH2:17]4)[NH:27][C:26]=2[C:25](=[O:28])[N:24]1[CH2:29][CH2:30][CH3:31]

Participants

5

Reactant 3

HCID 962WaterHCID 76113Bromotrimethylsilane2×HCID 86591743HCID 86591743, compound

Product 1

HCID 18767628HCID 18767628, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of {2-[4-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]oct-1-yl]-ethyl}-phosphonic acid diethyl ester (30 mg, 59 μmol) in CH2Cl2 (8 ml) was added TMSBr (excess) and the resulting mixture was stirred at rt overnight. Additional TMSBr was added and the reaction was heated at 55° C. for 6 h. The solvent was removed in vacuo to give an orange solid whose color was discharged upon trituration with water. The material was collected, washed with water and dried (20 mg, 77%). MS: 453 (MH+).

Workup

  1. temperaturethe reaction was heated at 55° C. for 6 h
  2. customThe solvent was removed in vacuo
  3. customto give an orange solid whose color
  4. customThe material was collected
  5. washwashed with water
  6. customdried (20 mg, 77%)

Sources & evidence

ORD record
ord-26e31192a92c43c28b5fef8974127095
Source dataset
uspto-grants-2009_08
Patent number
US07579354B2

Reaction notes

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