Dichloromethane → 5-Iodo-4-(methoxymethoxy)-2,6-dimethylpyrimidine

HRID 2387748Notes

Reaction equation

C(N(CC)C(C)C)(C)C.ClCCl.[I:13][C:14]1[C:15]([OH:22])=[N:16][C:17]([CH3:21])=[N:18][C:19]=1[CH3:20].[CH3:23][O:24][CH2:25]Cl>O>[I:13][C:14]1[C:15](=[O:22])[N:16]([CH2:23][O:24][CH3:25])[C:17]([CH3:21])=[N:18][C:19]=1[CH3:20].[I:13][C:14]1[C:15]([O:22][CH2:23][O:24][CH3:25])=[N:16][C:17]([CH3:21])=[N:18][C:19]=1[CH3:20]

Participants

Conditions

Temperature: -40 °C

Procedure

N,N-diisopropylethylamine (13.1 ml) was added to a dichloromethane (100 ml) solution of the compound 326-2 (14.5 g). Chloromethyl methyl ether (4.85 ml) was added to the reaction solution, while the solution was stirred at −40° C. The obtained mixture was stirred at room temperature for 15 hours. Water was added to the reaction solution, and the mixture was extracted with dichloromethane. The obtained organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-heptane:ethyl acetate=19:1 to 0:1), so as to obtain the title compound (10.6 g) and 5-iodo-4-(methoxymethoxy)-2,6-dimethylpyrimidine (2.55 g).

Workup

stirringThe obtained mixture was stirred at room temperature for 15 hours
extractionthe mixture was extracted with dichloromethane
dry with materialThe obtained organic layer was dried over magnesium sulfate
concentrationconcentrated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (n-heptane:ethyl acetate=19:1 to 0:1)

Sources & evidence

ORD record: ord-6596d1464a1c458f808f6a3bc5bba5f9
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268848B2

Reaction notes

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