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

HRID 2387748
Notes
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Reaction equation

HRID 2387748 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 178432770HCID 178432770, compound

Product 2

HCID 672831815-Iodo-4-(methoxymethoxy)-2,6-dimethylpyrimidineHCID 674740695-iodo-3-(methoxymethyl)-2,6-dimethylpyrimidin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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

  1. stirringThe obtained mixture was stirred at room temperature for 15 hours
  2. extractionthe mixture was extracted with dichloromethane
  3. dry with materialThe obtained organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes