Methoxymethyl-triphenylphosphonium chloride → HCID 18173042, compound

HRID 395885Notes

Reaction equation

[Cl-].[CH3:2][O:3]C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].O=[C:35]1[CH:40]2[CH2:41][CH2:42][CH:36]1[CH2:37][CH:38]([C:43]1[NH:51][C:50]3[C:49](=[O:52])[N:48]([CH2:53][CH2:54][CH3:55])[C:47](=[O:56])[N:46]([CH2:57][CH2:58][CH3:59])[C:45]=3[N:44]=1)[CH2:39]2>C1(C)C=CC=CC=1>[O:56]=[C:47]1[N:46]([CH2:57][CH2:58][CH3:59])[C:45]2[N:44]=[C:43]([CH:38]3[CH2:37][CH:36]4[CH:35]([CH:2]=[O:3])[CH:40]([CH2:41][CH2:42]4)[CH2:39]3)[NH:51][C:50]=2[C:49](=[O:52])[N:48]1[CH2:53][CH2:54][CH3:55]

Participants

Conditions

Temperature: 0 °C

Procedure

(Methoxymethyl)triphenylphosphonium chloride (296 mg 0.86 mmol) in toluene was cooled in an ice-bath. Potassium bis(trimethylsilyl)amide (2.5 ml, 0.5M in toluene) was added dropwise through a syringe. The mixture was stirred at 0° C. for 1 h. 8-(8-Oxo-bicyclo[3.2.1]oct-3-yl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dione (100 mg) was then added to the mixture, and the mixture was allowed to warm to room temperature and was stirred overnight. Toluene was evaporated off, and the residue was treated with 1N HCl in THF at 70° C. for 3 h. Ethyl acetate was used to extract the product. Column chromatography gave 94 mg of 3-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[3.2.1]octane-8-carbaldehyde as a mixture of cis and trans yield (90%)

Workup

temperatureto warm to room temperature
stirringwas stirred overnight
customToluene was evaporated off
additionthe residue was treated with 1N HCl in THF at 70° C. for 3 h
extractionto extract the product

Sources & evidence

ORD record: ord-467b8ab438a443e88afa1adf818f91ae
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06605600B1

Reaction notes

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