Water → 2-[[(2,3-Difluorophenyl)methyl]sulfonyl]-4-[[-2-hydroxy-1-hydroxymethylethyl]amino]-7(8H)-pteridinone

HRID 2105158Notes

Reaction equation

HRID 2105158 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][S:10][C:11]1[N:20]=[C:19]([NH:21][CH:22]([CH2:25][OH:26])[CH2:23][OH:24])[C:18]2[N:17]=[CH:16][C:15](=[O:27])[NH:14][C:13]=2[N:12]=1.[OH2:28].[OH:29]OS([O-])=O.[K+]>C(#N)C>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][S:10]([C:11]1[N:20]=[C:19]([NH:21][CH:22]([CH2:25][OH:26])[CH2:23][OH:24])[C:18]2[N:17]=[CH:16][C:15](=[O:27])[NH:14][C:13]=2[N:12]=1)(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 962WaterHCID 225059782-[[(2,3-Difluorophenyl)methyl]thio]4-[[2-hydroxy-1-(hydroxymethyl)ethyl]amino]-7(8H)-pteridinoneHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 225059372-[[(2,3-Difluorophenyl)methyl]sulfonyl]-4-[[-2-hydroxy-1-hydroxymethylethyl]amino]-7(8H)-pteridinone

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-[[(2,3-Difluorophenyl)methyl]thio]-4-[[-2-hydroxy-1-hydroxymethylethyl]amino]-7(8H)-pteridinone (2.25 g) was stirred in acetonitrile (750 ml) and water (750 ml) with oxone (22.5 g) for 18 hrs. Acetonitrile was removed in vacuo to leave an aqueous suspension. The mixture was extracted into ethyl acetate. The combined extracts were washed with saturated sodium chloride solution, dried (MgSO4) and the solvent removed in vacuo to afford the subtitled compound (1.92 g).

Workup

  1. customAcetonitrile was removed in vacuo
  2. customto leave an aqueous suspension
  3. extractionThe mixture was extracted into ethyl acetate
  4. washThe combined extracts were washed with saturated sodium chloride solution
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-2d8fe9402e314207a48ae185f8f324bb
Source dataset
uspto-grants-2009_08
Patent number
US07579342B2

Reaction notes

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