Water → 2-Chloro-4-[(3S)-3-methylmorpholin-4-yl]-6-[(4-methyl-1,3-thiazol-2-yl)sulfonylmethyl]pyrimidine

HRID 2353756Notes

Reaction equation

HRID 2353756 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([CH2:9][S:10]([C:13]2[S:14][CH:15]=[C:16]([CH3:18])[N:17]=2)(=[O:12])=[O:11])[N:3]=1.C(N(CC)CC)C.[CH3:26][C@H:27]1[CH2:32][O:31][CH2:30][CH2:29][NH:28]1.O>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]([N:28]2[CH2:29][CH2:30][O:31][CH2:32][C@@H:27]2[CH3:26])[CH:5]=[C:4]([CH2:9][S:10]([C:13]2[S:14][CH:15]=[C:16]([CH3:18])[N:17]=2)(=[O:12])=[O:11])[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 12012220(3S)-3-methylmorpholineHCID 593801702,4-Dichloro-6-[(4-methyl-1,3-thiazol-2-yl)sulfonylmethyl]pyrimidine

Product 1

HCID 593801542-Chloro-4-[(3S)-3-methylmorpholin-4-yl]-6-[(4-methyl-1,3-thiazol-2-yl)sulfonylmethyl]pyrimidineYield 56.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cooled (ice/water bath) solution of 2,4-dichloro-6-[(4-methyl-1,3-thiazol-2-yl)sulfonylmethyl]pyrimidine (901 mg, 2.78 mmol) in DCM (12 mL) was added triethylamine (0.45 mL, 3.23 mmol). The resulting solution was treated dropwise, over 3 minutes, with a solution of (3S)-3-methylmorpholine (319 mg, 3.15 mmol) in DCM (2.5 mL). The reaction mixture was stirred, under nitrogen for 24 hours, allowing reaction to warm to RT. Water (20 mL) was added to reaction mixture and stirred for 15 minutes. The organic layer was then separated, dried (MgSO4) and evaporated to give crude product, which was purified by flash silica chromatography, elution gradient 25 to 75% ethyl acetate in isohexane, to give the desired material (615 mg).

Workup

  1. customreaction
  2. stirringstirred for 15 minutes
  3. customThe organic layer was then separated
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customto give crude product, which
  7. customwas purified by flash silica chromatography, elution gradient 25 to 75% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-770d27b01e0f42ec8dcfebdc4eff1998
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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