Triethylamine → HCID 86704217, compound

HRID 624060Notes

Reaction equation

HRID 624060 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([CH2:11][CH2:12][CH2:13][OH:14])[N:4]=1.CCN(CC)CC.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>C(Cl)Cl>[CH3:22][S:23]([O:14][CH2:13][CH2:12][CH2:11][C:5]1[N:6]=[C:7]([O:9][CH3:10])[CH:8]=[C:3]([O:2][CH3:1])[N:4]=1)(=[O:25])=[O:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68283390HCID 68283390, compound

Product 1

HCID 86704217HCID 86704217, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(4,6-dimethoxypyrimidin-2-yl)propan-1-ol (100 mg, 0.50 mmol) in DCM (2.0 mL), Et3N (0.21 mL, 1.51 mmol) was added. After stirring for 5 min at rt, the reaction mixture was cooled to 0° C. and methansulfonylchloride (0.05 mL, 0.61 mmol) was added. The reaction mixture was stirred for 10 min at 0° C. and for 20 min at rt, then poured onto ice water. The aq. layer was extracted with DCM, the org. layer was washed with 1 N aq. HCl-solution followed by sat. NaHCO3-solution, then dried (MgSO4), filtered and the solvent was removed under reduced pressure to yield the tiltle compound as a yellow oil which was used immediately in the next step. The LC-MS conditions B: tR=0.60 min, [M+H]+=277.09.

Workup

  1. temperaturethe reaction mixture was cooled to 0° C.
  2. stirringThe reaction mixture was stirred for 10 min at 0° C. and for 20 min at rt
  3. additionpoured onto ice water
  4. extractionThe aq. layer was extracted with DCM
  5. washlayer was washed with 1 N aq. HCl-solution
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-6fe78feb930848b7bf9c2a4d2bc951a9
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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