Methyl Methanesulfonate → 1-(2-Hydroxyethyl)-2-methylthio-3,4,5,6-tetrahydropyrimidine mesylate

HRID 256538

Reaction equation

HRID 256538 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][CH2:7][NH:6][C:5]1=[S:10].[CH3:11][S:12]([O:15]C)(=[O:14])=[O:13]>C(O)C.COC(C)(C)C>[S:12]([OH:15])(=[O:14])(=[O:13])[CH3:11].[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][CH2:7][NH:6][CH:5]1[S:10][CH3:11]

Participants

5

Reactant 2

HCID 4156Methyl MethanesulfonateHCID 36032811-(2-Hydroxyethyl)-3,4,5,6-tetrahydropyrimidine-2-thione

Product 1

HCID 867473441-(2-Hydroxyethyl)-2-methylthio-3,4,5,6-tetrahydropyrimidine mesylateYield 128.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

Then, 1-(2-hydroxyethyl)-3,4,5,6-tetrahydropyrimidine-2-thione (121.2 g) and methyl methanesulfonate (91.51 g) are heated at reflux in ethyl alcohol (200 ml) for about 2 hours and then allowed to cool to room temperature. The mixture was diluted with t-butyl methyl ether (2 liters). An oil separates which crystallizes on keeping in freezer at -20° C. Filtration and drying yields 145.7 g of 1-(2-hydroxyethyl)-2-methylthio-3,4,5,6-tetrahydropyrimidine mesylate, melting point 61.7°-62.2° C.

Workup

  1. customAn oil separates which crystallizes
  2. customon keeping in freezer at -20° C
  3. filtrationFiltration
  4. customdrying

Sources & evidence

ORD record
ord-333625bfe3524323baec2a941c41e1f7
Source dataset
uspto-grants-1993_11
Patent number
US05258381

Linked notes

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