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

HRID 397273노트

반응식

HRID 397273 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a15a4876092e411db99ec11eebdfd553
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06610518B2

반응 노트

불러오는 중…