Methanesulfonyl chloride → HCID 13279244, compound

HRID 542381Notes

Reaction equation

HRID 542381 reaction equation
[CH2:1]([N:4]([C:9]1[C:10]([CH3:19])=[N:11][C:12]([N:16]([CH3:18])[CH3:17])=[N:13][C:14]=1[CH3:15])[C:5](=[O:8])[CH2:6]O)[C:2]#[CH:3].S([Cl:24])(C)(=O)=O>CN(C)C1C=CN=CC=1.C(Cl)Cl.O>[CH2:1]([N:4]([C:9]1[C:10]([CH3:19])=[N:11][C:12]([N:16]([CH3:18])[CH3:17])=[N:13][C:14]=1[CH3:15])[C:5](=[O:8])[CH2:6][Cl:24])[C:2]#[CH:3]

Participants

6

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 13279243HCID 13279243, compound

Product 1

HCID 13279244HCID 13279244, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

8.0 g of N-propargyl-N-(4,6-dimethyl-2-dimethylamino-pyrimidin-5-yl)-hydroxyacetamide, 3.7 g 4-dimethylaminopyridine and 100 ml dry CH2Cl2 are charged in a sulphonation flask. Thereto are added, dropwise, 3.43 g mesyl chloride in 30 ml of dry CH2Cl2. The reaction temperature rises from 22° up to 33°. The mixture is heated under reflux for 34 hours, cooled and diluted with water. The organic phase is partitioned off, dried over Na2SO4 and evaporated. The oily residue is chromatographed on silica gel with diethylether/hexane 1:1 to give the title compound, m.p. 108°-110°.

Workup

  1. additionThereto are added
  2. customrises from 22° up to 33°
  3. temperatureThe mixture is heated
  4. temperatureunder reflux for 34 hours
  5. temperaturecooled
  6. customThe organic phase is partitioned off
  7. dry with materialdried over Na2SO4
  8. customevaporated
  9. customThe oily residue is chromatographed on silica gel with diethylether/hexane 1:1

Sources & evidence

ORD record
ord-166bcbc52c784528add8f0d3e14151ad
Source dataset
uspto-grants-1987_04
Patent number
US04657579

Reaction notes

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