Morpholine → HCID 59379935, compound

HRID 2353642Notes

Reaction equation

HRID 2353642 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([CH2:9][S:10]([CH3:13])(=[O:12])=[O:11])[N:3]=1.C(N(CC)CC)C.[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1>C(Cl)Cl>[Cl:1][C:2]1[N:3]=[C:4]([CH2:9][S:10]([CH3:13])(=[O:12])=[O:11])[CH:5]=[C:6]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[N:7]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 574276252,4-Dichloro-6-((methylsulfonyl)methyl)pyrimidine

Product 1

HCID 59379935HCID 59379935, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-5 °C

Procedure

A suspension of 2,4-dichloro-6-(methylsulfonylmethyl)pyrimidine (10.56 g) in DCM (230 mL) was stirred magnetically (under nitrogen) and cooled to −5° C. Triethylamine (6.78 mL) was added followed by the dropwise addition of a solution of morpholine (3.85 mL) in DCM (30 mL) maintaining the reaction temperature below −5° C. The reaction was stirred at room temperature for 1 hour and then the organic mixture washed with water (300 mL). The organic phase was dried (MgSO4), filtered and evaporated to a brown solid which was chromatographed on silica, eluting with 50% ethyl acetate in DCM, to give the desired material (6.81 g) as a white solid.

Workup

  1. temperaturemaintaining the reaction temperature below −5° C
  2. stirringThe reaction was stirred at room temperature for 1 hour
  3. washthe organic mixture washed with water (300 mL)
  4. dry with materialThe organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated to a brown solid which
  7. customwas chromatographed on silica
  8. washeluting with 50% ethyl acetate in DCM

Sources & evidence

ORD record
ord-7270175e13ef4bf69f933b203a3ffddc
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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