Methanol → N-[6-methoxy-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-4,4-dimethyl-1-pentanesulfonamide

HRID 397272Notes

Reaction equation

HRID 397272 reaction equation
[H-].[Na+].Cl[C:4]1[N:9]=[C:8]([C:10]2[N:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[N:7]=[C:6]([NH:16][S:17]([CH2:20][CH2:21][CH2:22][C:23]([CH3:26])([CH3:25])[CH3:24])(=[O:19])=[O:18])[C:5]=1[O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[O:34][CH3:35].[CH3:36][OH:37]>>[CH3:36][O:37][C:4]1[N:9]=[C:8]([C:10]2[N:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[N:7]=[C:6]([NH:16][S:17]([CH2:20][CH2:21][CH2:22][C:23]([CH3:26])([CH3:25])[CH3:24])(=[O:19])=[O:18])[C:5]=1[O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[O:34][CH3:35]

Participants

4

Reactant 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 22999698N-[6-chloro-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-4,4-dimethyl-1-pentanesulfonamide

Product 1

HCID 22999699N-[6-methoxy-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-4,4-dimethyl-1-pentanesulfonamide

Conditions

Temperature
105 °C

Procedure

Sodium hydride (60% oil dispersion 354 mg) was cautiously added to a suspension of N-[6-chloro-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-4,4-dimethyl-1-pentanesulfonamide (580 mg) in dry methanol (5 ml) in a 10 mm Wheaton reacti-vial™ and the resulting mixture stirred at 105° C. for 4 hours. The reaction was then partitioned between ethyl acetate (20 ml) and 2N aqueous hydrochloric acid (10 ml) and the organic phase separated. The aqueous was extracted with ethyl acetate (20 ml ) and the organic phases combined, washed (water 2×20 ml), dried (Na2SO4) and evaporated under reduced pressure. Column chromatography on silica eluting with a solvent gradient of dichloromethane:methanol 100:0 changing to 98.5:1.5 gave N-[6-methoxy-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-4,4-dimethyl-1-pentanesulfonamide as an off-white coloured solid (189 mg).

Workup

  1. customThe reaction was then partitioned between ethyl acetate (20 ml) and 2N aqueous hydrochloric acid (10 ml)
  2. customthe organic phase separated
  3. extractionThe aqueous was extracted with ethyl acetate (20 ml )
  4. washwashed (water 2×20 ml)
  5. dry with materialdried (Na2SO4)
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-817519a50f58474ea54b89b6a21cf8de
Source dataset
uspto-grants-2003_08
Patent number
US06610518B2

Reaction notes

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