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

HRID 602302
Notes
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Reaction equation

HRID 602302 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 8028TetrahydrofuranSolvent
HCID 8857
Ethyl Acetate
Solvent

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-f29129d4ead6479bacd24545ca5fd1f4
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07906511B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes