4,6-Dichloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidine → N-[6-chloro-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-3,3-dimethyl-1-butanesulfonamide

HRID 397271Notes

Reaction equation

HRID 397271 reaction equation
[K].[CH3:2][C:3]([CH3:11])([CH3:10])[CH2:4][CH2:5][S:6]([NH2:9])(=[O:8])=[O:7].[Cl:12][C:13]1[C:18]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[O:26][CH3:27])=[C:17](Cl)[N:16]=[C:15]([C:29]2[N:34]=[CH:33][CH:32]=[CH:31][N:30]=2)[N:14]=1>CS(C)=O>[Cl:12][C:13]1[N:14]=[C:15]([C:29]2[N:34]=[CH:33][CH:32]=[CH:31][N:30]=2)[N:16]=[C:17]([NH:9][S:6]([CH2:5][CH2:4][C:3]([CH3:11])([CH3:10])[CH3:2])(=[O:8])=[O:7])[C:18]=1[O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[O:26][CH3:27]

Participants

4

Reactant 2

HCID 105457064,6-Dichloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidineHCID 86584254HCID 86584254, compound

Product 1

HCID 22999716N-[6-chloro-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-3,3-dimethyl-1-butanesulfonamideYield 91.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

3,3-dimethylbutane-1-sulphonic acid amide potassium salt (616 mg) was added to a solution of 4,6-dichloro-5-(2-methoxyphenoxy)-2-(pyrimidin-2-yl)-pyrimidine (Can. Pat. Appl. 2071193) (353 mg) in dry dimethyl sulphoxide (10 ml) and the resulting mixture stirred at 120° C. for 6 hours under nitrogen. The reaction mixture was allowed to cool and then partitioned between ethyl acetate (30 ml ) and 2N aqueous hydrochloric acid (30 ml ) and the organic phase separated. The aqueous was extracted with ethyl acetate (30 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 pentane:ethyl acetate 50:50 changing to 0:100 and finally ethyl acetate:methanol 98:2 gave N-[6-chloro-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-3,3-dimethyl-1-butanesulfonamide as an off-white solid (440 mg).

Workup

  1. temperatureto cool
  2. custompartitioned between ethyl acetate (30 ml ) and 2N aqueous hydrochloric acid (30 ml )
  3. customthe organic phase separated
  4. extractionThe aqueous was extracted with ethyl acetate (30 ml)
  5. washwashed (water 2×20 ml)
  6. dry with materialdried (Na2SO4)
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-30c34ececcdd4d66b795029e5784d4e9
Source dataset
uspto-grants-2003_08
Patent number
US06610518B2

Reaction notes

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