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Diethyl Ether → 2,5-Dichloro-4-methoxypyrimidine

HRID 1630333
Notes
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Reaction equation

HRID 1630333 reaction equation
[Cl:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[CH2:10]([O:12]CC)C.C[O-].[Na+]>CO>[Cl:8][C:5]1[N:4]=[C:3]([O:12][CH3:10])[C:2]([Cl:1])=[CH:7][N:6]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 2372592,4,5-TrichloropyrimidineHCID 10942334Sodium Methoxide

Product 1

HCID 497617462,5-Dichloro-4-methoxypyrimidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a 250 mL round bottom flask equipped with a stir bar was added 1 g 5-chloro-2,4-dichloro-pyrimidine, and 15 mL of diethyl ether. The mixture was cooled to 0° C. in an ice bath and then 1 equivalent of sodium methoxide in methanol (prepared from reacting 120 mg of sodium with 4 mL of methanol at room temperature) was slowly added. The reaction was stirred over night at room temperature and checked by LCMS. The white precipitate was filtered and the solid washed with cold methanol. After drying, 0.98 g of pure 2,5-dichloro-4-methoxypyrimidine was obtained and this material was used without further purification.

Workup

  1. customTo a 250 mL round bottom flask equipped with a stir bar
  2. filtrationThe white precipitate was filtered
  3. washthe solid washed with cold methanol
  4. customAfter drying

Sources & evidence

ORD record
ord-87606e4e32654582b4d49afdfbb179d0
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08791130B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes