Cesium carbonate → N-[6-chloro-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-4,4-dimethyl-1-pentanesulfonamide

HRID 397273Notes

Reaction equation

HRID 397273 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:7][C:8]([CH3:17])([CH3:16])[CH2:9][CH2:10][CH2:11][S:12]([NH2:15])(=[O:14])=[O:13].[Cl:18][C:19]1[C:24]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[O:32][CH3:33])=[C:23](Cl)[N:22]=[C:21]([C:35]2[N:40]=[CH:39][CH:38]=[CH:37][N:36]=2)[N:20]=1>CN(C)C=O>[Cl:18][C:19]1[N:20]=[C:21]([C:35]2[N:40]=[CH:39][CH:38]=[CH:37][N:36]=2)[N:22]=[C:23]([NH:15][S:12]([CH2:11][CH2:10][CH2:9][C:8]([CH3:17])([CH3:16])[CH3:7])(=[O:14])=[O:13])[C:24]=1[O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[O:32][CH3:33]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 105457064,6-Dichloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidineHCID 865842554,4-Dimethylpentane-1-sulfonamide

Product 1

HCID 22999698N-[6-chloro-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-4,4-dimethyl-1-pentanesulfonamideYield 54.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Caesium carbonate (2.62 g) was added to a solution of 4,4-dimethylpentane-1-sulphonic acid amide (720 mg) and 4,6-dichloro-5-(2-methoxyphenoxy)-2-(pyrimidin-2-yl)-pyrimidine (Can. Pat. Appl. 2071193) (1.40 g) in dry N,N-dimethyl formamide (8 ml) and the resulting mixture stirred at 80° C. for 4 hours under nitrogen. The reaction mixture was allowed to cool and then partitioned between ethyl acetate (40 ml) and 2N aqueous hydrochloric acid (20 ml). The organic phase was separated, washed (brine 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 99:1 gave crude product which was recrystallised from ethyl acetate:pentane to give N-[6-chloro-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-4,4-dimethyl-1-pentanesulfonamide as a white solid (1.08 g).

Workup

  1. temperatureto cool
  2. custompartitioned between ethyl acetate (40 ml) and 2N aqueous hydrochloric acid (20 ml)
  3. customThe organic phase was separated
  4. washwashed (brine 2×20 ml)
  5. dry with materialdried (Na2SO4)
  6. customevaporated under reduced pressure
  7. customColumn chromatography on silica eluting with a solvent gradient of dichloromethane:methanol 100:0 changing to 99:1 gave crude product which
  8. customwas recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-a15a4876092e411db99ec11eebdfd553
Source dataset
uspto-grants-2003_08
Patent number
US06610518B2

Reaction notes

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