3,4-dihydro-2H-pyran → HCID 19735313, compound

HRID 326704Notes

Reaction equation

HRID 326704 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[N:10]=[CH:9][N:8]=[C:7]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([CH:21]=[CH2:22])=[CH:17][CH:16]=2)(=[O:14])=[O:13])[C:6]=1[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[O:30][CH3:31].[O:32]1[CH:37]=[CH:36][CH2:35][CH2:34][CH2:33]1>O1CCCC1.FC(F)(F)C(O)=O>[CH3:31][O:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[CH2:23][C:6]1[C:7]([NH:11][S:12]([C:15]2[CH:16]=[CH:17][C:18]([CH:21]=[CH2:22])=[CH:19][CH:20]=2)(=[O:13])=[O:14])=[N:8][CH:9]=[N:10][C:5]=1[O:4][CH2:3][CH2:2][O:1][CH:33]1[CH2:34][CH2:35][CH2:36][CH2:37][O:32]1

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 19735533HCID 19735533, compound

Product 1

HCID 19735313HCID 19735313, compound

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 110 mg of N-[6-(2-hydroxyethoxy)-5-(o-methoxybenzyl)-4-pyrimidinyl]-p-vinylbenzenesulfonamide in 3 ml of absolute tetrahydrofuran was treated with 0.3 ml of 3,4-dihydro-2H-pyran and 4 drops of trifluoroacetic acid. After boiling under reflux overnight, the solvent was distilled under reduced pressure and the residue was chromatographed on silica gel with methylene chloride/ethyl acetate (9:1). There were obtained 100 mg of rac-N-[5-(o-methoxybenzyl)-6-[2-[(tetrahydro-2H-pyran-2-yl)oxy]ethoxy]-4-pyrimidinyl]-p-vinylbenzenesulfonamide as a white resin, MS: 460 (M--SO2 +H); 430 (M--SO2 +OCH3).

Workup

  1. temperatureunder reflux overnight
  2. distillationthe solvent was distilled under reduced pressure
  3. customthe residue was chromatographed on silica gel with methylene chloride/ethyl acetate (9:1)

Sources & evidence

ORD record
ord-b175c743d4214256ae0e02954f40b92c
Source dataset
uspto-grants-1993_12
Patent number
US05270313

Reaction notes

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