Bromotrimethylsilane → HCID 19993501, compound

HRID 345086Notes

Reaction equation

HRID 345086 reaction equation
Br[Si](C)(C)C.C([O:8][P:9]([CH2:14][O:15][CH2:16][CH:17]([OH:30])[CH2:18][O:19][N:20]1[CH:28]=[N:27][C:26]2[C:21]1=[N:22][CH:23]=[N:24][C:25]=2[NH2:29])([O:11]CC)=[O:10])C>ClCCl>[OH:30][CH:17]([CH2:16][O:15][CH2:14][P:9]([OH:10])([OH:11])=[O:8])[CH2:18][O:19][N:20]1[CH:28]=[N:27][C:26]2[C:21]1=[N:22][CH:23]=[N:24][C:25]=2[NH2:29]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 19993537HCID 19993537, compound

Product 1

HCID 19993501HCID 19993501, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

Bromotrimethylsilane (1.4 ml, 10.6 mmol) was added to a solution of 9-[3-(diethoxyphosphorylmethoxy)-2-hydroxypropoxy]adenine (200 mg, 0.52 mmol) in dichloromethane (8 ml) and stirred under nitrogen for 16 h at 20° C. The solvents were evaporated in vacuo, co-evaporating the residue with methanol and toluene. The residue was recrystallised from water-acetone 1:1, affording 9-[2-hydroxy-3-(phosphonomethoxy)propoxy]adenine (130 mg, 76%) as a white solid m.p. 218°-221° C. λmax (H2O), 259 (ε13,500)nm; νmax (KBr) 3400, 1700 and 1620 cm-1 ; δH [(CD3)2SO] 3.59 (4H, m, CH2OCH2P), 3.95 (1H, m, CH,OH), 4.27 (1H, m, CH2ON), 4.39 (1H, m, CH2ON), 7.43 (2H, br.s, D2O exchangeable, NH2), 8.16 (1H, s, H-2/H-8), 8.39 (1H, s, H-2/H-8); m/z (FAB+ve Ion), 320 (MH+). Found: C, 33.79; H, 4.79; N, 22.00%; C9H14N5O6P requires C, 33.86; H, 4.42; N, 21.94%.

Workup

  1. customThe solvents were evaporated in vacuo
  2. customThe residue was recrystallised from water-acetone 1:1

Sources & evidence

ORD record
ord-f9a4d6de9a854cb1898d7fe71abe61ac
Source dataset
uspto-grants-1991_10
Patent number
US05055458

Reaction notes

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