2-(4-Bromophenyl)pyrimidin-5-ol → 2-(4-(Methylsulfonyl)phenyl)pyrimidin-5-ol

HRID 423571Notes

Reaction equation

HRID 423571 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][C:11]([OH:14])=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[Na+].[CH3:16][S:17]([O-:19])=[O:18]>CS(C)=O>[CH3:16][S:17]([C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][C:11]([OH:14])=[CH:10][N:9]=2)=[CH:4][CH:3]=1)(=[O:19])=[O:18]

Participants

4

Reactant 2

HCID 6199082-(4-Bromophenyl)pyrimidin-5-olHCID 2733271Sodium methanesulfinate

Product 1

HCID 666730022-(4-(Methylsulfonyl)phenyl)pyrimidin-5-olYield 24.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-[4-(Methylsulfonyl)phenyl]-5-pyrimidinol (0.19 g, 40%) was prepared as a light brown solid from 2-(4-bromophenyl)-pyrimidin-5-ol (0.50 g, 1.89 mmol), methanesulfinic acid sodium salt (0.73 g, 80%, 5.68 mmol) and Cul (1.08 g, 5.68 mmol) in DMSO (15 mL) in a manner similar to Example 83, Step 2. The crude product was purified by chromatography on a silica gel column eluted with 2:4:0.1 EtOAc/CH2Cl2/MeOH to give 0.116 g 2-[4-(methylsulfonyl)phenyl]-5-pyrimidinol as a light brown solid. Impure fractions were combined and further purified by chromatography on a silica gel column eluted with 2:6:0.1 EtOAc/CH2Cl2/MeOH to give additional 0.075 g of 2-[4-(methylsulfonyl)phenyl]-5-pyrimidinol as a light brown solid (40% yield overall). 1H NMR (400 MHz, DMSO-d6): δ 10.82 (s, 1H), 8.60-8.40 (m, 4H), 8.00 (d, 2H, J=8.5 Hz), 3.23 (s, 3H); LRMS (ESI), m/z 251 (M+H).

Workup

  1. customThe crude product was purified by chromatography on a silica gel column
  2. washeluted with 2:4:0.1 EtOAc/CH2Cl2/MeOH

Sources & evidence

ORD record
ord-0efacee5fb5343b5b0c3628277d4bc93
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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