Triethylamine → HCID 178460599, compound

HRID 2171325Notes

Reaction equation

HRID 2171325 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N:8]([CH:10]([CH3:13])[CH2:11][OH:12])[CH3:9])[NH:5][C:4](=[O:14])[N:3]=1.C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>O1CCCC1>[CH3:22][S:23]([O:12][CH2:11][CH:10]([N:8]([C:6]1[NH:5][C:4](=[O:14])[N:3]=[C:2]([Cl:1])[CH:7]=1)[CH3:9])[CH3:13])(=[O:25])=[O:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178460128HCID 178460128, compound

Product 1

HCID 178460599HCID 178460599, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4-chloro-6-((1-hydroxypropan-2-yl)(methyl)amino)pyrimidin-2(1H)-one (1.0 g, 4.6 mmol) and triethylamine (1.9 mL, 14 mmol) in tetrahydrofuran (THF) (15 mL) was added MsCl (0.72 mL, 9.2 mmol) at 0˜5° C. The reaction mixture was stirred at room temperature overnight, and then quenched with 1 M NaHCO3 solution, diluted with water and extracted with ethyl acetate. Combined organic parts were dried over anhydrous Na2SO4, filtered and concentrated to give the residue as yellow oil. The crude was used into next step without further purification.

Workup

  1. customquenched with 1 M NaHCO3 solution
  2. additiondiluted with water
  3. extractionextracted with ethyl acetate
  4. dry with materialCombined organic parts were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9262213e9b4b4c8b9c1a086deb94fb5d
Source dataset
uspto-grants-2015_06
Patent number
US09051325B2

Reaction notes

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