Pyridine → HCID 58089387, compound

HRID 1966335Notes

Reaction equation

HRID 1966335 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[N:14]=[C:13]([OH:21])[C:12]=2[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[C:28]1([S:38](Cl)(=[O:40])=[O:39])[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=[CH:30][CH:29]=1.N1C=CC=CC=1>ClCCl>[C:28]1([S:38]([O:21][C:13]2[C:12]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:11]([C:8]3[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:10][CH:9]=3)[N:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[N:14]=2)(=[O:40])=[O:39])[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 665601-Naphthalenesulfonyl chlorideHCID 178504693HCID 178504693, compound

Product 1

HCID 58089387HCID 58089387, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 6-[4-(methylsulfonyl)phenyl]-5-phenyl-2-(trifluoromethyl)pyrimidin-4-ol (0.1 g, 0.25 mmol, prepared according to the procedure described in PCT/IB03/01289) in dichloromethane (10 ml) was added naphthalene-1-sulfonyl chloride (0.086 g, 0.37 mmol) in dichloromethane (4 ml) at 0° C. and the mixture was stirred for 10 minutes. Subsequently pyridine (0.04 ml, 0.5 mmol) was added under stirring and the stirring was continued further for 6 hours at 37° C. Dichloromethane was removed under vacuo and the resultant mixture was diluted with water:ethyl:acetate (1:1, 100 ml) and then extracted with ethyl acetate (3×25 ml). The organic layer was washed with brine (100 ml), dried over anhydrous sodium sulphate and evaporated to afford the title compound (0.096 g, yield 67%); m.p. 204-206° C. 1H-NMR (CDCl3) δ: 2.99 (s, 3H), 7.12-7.14 (d, 2H), 7.26-7.29 (dd, 3H), 7.37-7.39 (m, 2H), 7.48-7.50 (m, 2H), 7.61-7.64 (m, 3H), 7.77-7.79 (d, 2H), 7.84-7.86 (d, 2H), 7.94-7.96 (d, 2H); MS m/z: 585.1 (M++1).

Workup

  1. stirringunder stirring
  2. waitthe stirring was continued further for 6 hours at 37° C
  3. customDichloromethane was removed under vacuo
  4. additionthe resultant mixture was diluted with water:ethyl:acetate (1:1, 100 ml)
  5. extractionextracted with ethyl acetate (3×25 ml)
  6. washThe organic layer was washed with brine (100 ml)
  7. dry with materialdried over anhydrous sodium sulphate
  8. customevaporated

Sources & evidence

ORD record
ord-12b4b0b692b84feb8257f760e4119744
Source dataset
uspto-grants-2013_04
Patent number
US08420653B2

Reaction notes

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