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

HRID 397273ノート

反応式

HRID 397273 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-a15a4876092e411db99ec11eebdfd553
出典データセット
uspto-grants-2003_08
特許番号
US06610518B2

反応ノート

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