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

HRID 1814258Notes

Reaction equation

HRID 1814258 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-5ef264aec4134a5e8cde04ded7b7d5a5
Source dataset
uspto-grants-2005_04
Patent number
US06875868B2

Reaction notes

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