Methanesulfonyl chloride → 4-Pyrimidinemethanol, 2-amino-, 4-methanesulfonate

HRID 1890495Notes

Reaction equation

HRID 1890495 reaction equation
C(N(CC)C(C)C)(C)C.[CH3:10][S:11](Cl)(=[O:13])=[O:12].[NH2:15][C:16]1[N:21]=[C:20]([CH2:22][OH:23])[CH:19]=[CH:18][N:17]=1>O1CCCC1.C(OCC)(=O)C>[NH2:15][C:16]1[N:21]=[C:20]([CH2:22][O:23][S:11]([CH3:10])(=[O:13])=[O:12])[CH:19]=[CH:18][N:17]=1

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 2004934-Pyrimidinemethanol, 2-amino-

Product 1

HCID 579711404-Pyrimidinemethanol, 2-amino-, 4-methanesulfonateYield 53%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

N,N-Diisopropylethylamine (490 μL, 2.9 mmol) and methanesulfonyl chloride (110 μL, 1.5 mmol) were added to a suspension of 2-amino-4-hydroxymethylpyrimidine (170 mg, 1.3 mmol, Reference Compound No. 4-1) in anhydrous tetrahydrofuran (5.0 mL) under ice-cooling, and the mixture was stirred for 7 hours at room temperature. The reaction mixture was diluted with ethyl acetate (300 mL), washed with water (300 mL), and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, the precipitated solid was filtered off with ethyl acetate, and dried under reduced pressure to give 140 mg of the title Reference Compound as a white solid (Yield: 53%).

Workup

  1. washwashed with water (300 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. filtrationthe precipitated solid was filtered off with ethyl acetate
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-fc6cbc93284e4f85b5164f68976219c8
Source dataset
uspto-grants-2013_08
Patent number
US08507485B2

Reaction notes

Loading…