Water → HCID 18767628, compound

HRID 480149Notes

Reaction equation

HRID 480149 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-d1050eaa14164efca6ef3551f3cb33c4
Source dataset
uspto-grants-2003_11
Patent number
US06649600B1

Reaction notes

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