Diethyl Ether → HCID 54225005, compound

HRID 326706Notes

Reaction equation

HRID 326706 reaction equation
CO[C:3]1[CH:37]=[CH:36][CH:35]=[CH:34][C:4]=1[CH2:5][C:6]1[C:7]([NH:22][S:23]([C:26]2[CH:33]=[CH:32][C:29]([CH:30]=[O:31])=[CH:28][CH:27]=2)(=[O:25])=[O:24])=[N:8][CH:9]=[N:10][C:11]=1[O:12][CH2:13][CH2:14][O:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][O:17]1.[Mg].[CH3:39]I.[Cl-].[NH4+].[CH2:43]([O:45]CC)C>C(OCC)(=O)C.O1CCCC1>[OH:31][CH:30]([C:29]1[CH:28]=[CH:27][C:26]([S:23]([NH:22][C:7]2[C:6]([CH:5]([O:45][CH3:43])[C:4]3[CH:3]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[C:11]([O:12][CH2:13][CH2:14][O:15][CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][O:17]3)[N:10]=[CH:9][N:8]=2)(=[O:24])=[O:25])=[CH:33][CH:32]=1)[CH3:39]

Participants

8

Reactant 5

HCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 53682521HCID 53682521, compound

Product 1

HCID 54225005HCID 54225005, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

170 mg of rac-p-[[5-(o-methoxybenzyl)-6-[2-[(tetrahydro-2H-pyran-2-yl]oxy]ethoxy]-4-pyrimidinyl]sulfamoyl]benzaldehyde and, after 30 minutes, 1 ml of absolute tetrahydrofuran were added at room temperature to a Grignard solution prepared from 60 mg of magnesium and 0.15 ml of methyl iodide in diethyl ether. After stirring at room temperature for 3 hours, the reaction was interrupted by the addition of saturated ammonium chloride solution. The reaction mixture was diluted with ethyl acetate and the aqueous phase was extracted twice with ethyl acetate. The organic phase was washed with water and saturated NaCl solution, dried and evaporated under reduced pressure. The residue was chromatographed over 35 g of SiO2 with CH2Cl2 /ethyl acetate (8:2) and (1:1) and yielded 135 mg of p-[(RS)-1-hydroxyethyl]-N-[5-(methoxybenzyl)-6-[2-[[(RS)-tetrahydro-2H-pyran-2-yl]oxy]ethoxy]-4-pyrimidinyl]benzene-sulfonamide melting point >56° C. (sublimation).

Workup

  1. extractionthe aqueous phase was extracted twice with ethyl acetate
  2. washThe organic phase was washed with water and saturated NaCl solution
  3. customdried
  4. customevaporated under reduced pressure
  5. customThe residue was chromatographed over 35 g of SiO2 with CH2Cl2 /ethyl acetate (8:2) and (1:1)

Sources & evidence

ORD record
ord-21e9039c719743e6ae9a66cfcab37e35
Source dataset
uspto-grants-1993_12
Patent number
US05270313

Reaction notes

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