Bromotrimethylsilane → HCID 136088361, compound

HRID 345084Notes

Reaction equation

HRID 345084 reaction equation
Br[Si](C)(C)C.[NH2:6][C:7]1[N:15]=[C:14]2[C:10]([N:11]=[CH:12][N:13]2[O:16][CH2:17][CH:18]([OH:30])[CH2:19][O:20][CH2:21][P:22]([O:27]CC)([O:24]CC)=[O:23])=[C:9]([O:31]C)[N:8]=1>ClCCl>[OH:30][CH:18]([CH2:19][O:20][CH2:21][P:22]([OH:24])([OH:27])=[O:23])[CH2:17][O:16][N:13]1[CH:12]=[N:11][C:10]2[C:9](=[O:31])[NH:8][C:7]([NH2:6])=[N:15][C:14]1=2

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 19993505HCID 19993505, compound

Product 1

HCID 136088361HCID 136088361, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

Bromotrimethylsilane (1.43 ml, 10.9 mmol) was added to a solution of 2-amino-9-[3-(diethoxyphosphorylmethoxy)-2-hydroxypropoxy]-6-methoxypurine (220 mg, 0.54 mmol) in dichloromethane (10 ml) and then stirred at 20° C. for 16 h. The reaction mixture was evaporated in vacuo and co-evaporated with toluene. The residue was recrystallised from water-acetone affording 9-[2-hydroxy-3-(phosphonomethoxy)propoxy]guanine (131 mg, 72%) as a white solid m.p. 245°-247° C., decomp. λmax (H2O) 252 (ε13,200)nm; νmax (KBr) 3400, 3300, 1720, 1640, 1590 and 1380 cm-1 ; δH [(CD3)2SO] 3.58 (2H, m, CH2OCH2P), 3.60 (2H, d, J8.5 Hz, CH2P), 3.91 (1H, m, CHOH), 4.17 (1H, m, CH2ON), 4.30 (1H, m, CH2ON), 6.64 (2H, br.s, D2O exchangeable, NH2), 7.93 (1H, s, H-8), 10.63 (1H, br.s, D2O exchangeable, NH); m/z (FAB+ve Ion), 336 (MH+). Found: C, 32.32; H, 4.08; N, 20.66%; C9H14N5O7P requires C, 32.25; H, 4.21; N, 20.89%.

Workup

  1. customThe reaction mixture was evaporated in vacuo and co-evaporated with toluene
  2. customThe residue was recrystallised from water-acetone

Sources & evidence

ORD record
ord-ebd07a55ea8a4bbc9245de49d4fc45bf
Source dataset
uspto-grants-1991_10
Patent number
US05055458

Reaction notes

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