Methanol → N-[6-methoxy-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-3,3-dimethyl-1-butanesulfonamide

HRID 397270Notes

Reaction equation

HRID 397270 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][C:22]([CH3:25])([CH3:24])[CH3:23])(=[O:19])=[O:18])[C:5]=1[O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[O:33][CH3:34].[CH3:35][OH:36]>>[CH3:35][O:36][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][C:22]([CH3:25])([CH3:24])[CH3:23])(=[O:19])=[O:18])[C:5]=1[O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[O:33][CH3:34]

Participants

4

Reactant 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 22999716N-[6-chloro-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-3,3-dimethyl-1-butanesulfonamide

Product 1

HCID 22999702N-[6-methoxy-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-3,3-dimethyl-1-butanesulfonamide

Conditions

Temperature
100 °C

Procedure

Sodium hydride (80% oil dispersion 132 mg) was cautiously added to a suspension of N-[6-chloro-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-3,3-dimethyl-1-butanesulfonamide (Preparation 2)(420 mg) in dry methanol (12 ml) divided equally between two 10 ml Wheaton reacti-vials™, and the resulting mixtures stirred at 100° C. for 3 hours. The reactions were then combined and partitioned between ethyl acetate (40 ml) and 2N aqueous hydrochloric acid (20 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 99:1 changing to 97:3 gave N-[6-methoxy-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-3,3-dimethyl-1-butanesulfonamide as an off-white coloured foam (265 mg).

Workup

  1. custompartitioned between ethyl acetate (40 ml) and 2N aqueous hydrochloric acid (20 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-564d4e638a304322830c6488df1d1f5b
Source dataset
uspto-grants-2003_08
Patent number
US06610518B2

Reaction notes

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