Cesium carbonate → [6-(6-Amino-pyridin-3-yl)-2-morpholin-4-yl-pyrimidin-4-yl]-(6-methoxy-pyridin-3-yl)-amine

HRID 1512131

반응식

HRID 1512131 반응식
C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:54]1[N:59]=[C:58]([N:60]2[CH2:65][CH2:64][O:63][CH2:62][CH2:61]2)[N:57]=[C:56]([C:66]2[CH:67]=[CH:68][C:69]([NH2:72])=[N:70][CH:71]=2)[CH:55]=1.[CH3:73][O:74][C:75]1[N:80]=[CH:79][C:78]([NH2:81])=[CH:77][CH:76]=1>CC([O-])=O.CC([O-])=O.[Pd+2].C1COCC1>[NH2:72][C:69]1[N:70]=[CH:71][C:66]([C:56]2[N:57]=[C:58]([N:60]3[CH2:65][CH2:64][O:63][CH2:62][CH2:61]3)[N:59]=[C:54]([NH:81][C:78]3[CH:79]=[N:80][C:75]([O:74][CH3:73])=[CH:76][CH:77]=3)[CH:55]=2)=[CH:67][CH:68]=1

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 811216-Methoxy-3-pyridinylamineHCID 634876Binap, (A+-)-HCID 595075305-(6-Chloro-2-morpholin-4-ylpyrimidin-4-yl)pyridin-2-ylamine

생성물 1

HCID 59507565[6-(6-Amino-pyridin-3-yl)-2-morpholin-4-yl-pyrimidin-4-yl]-(6-methoxy-pyridin-3-yl)-amine수율 32.1%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 8028Tetrahydrofuran용매

실험 절차

In a glass pressure vessel, Pd(OAc)2 (2.0 mg, 0.0082 mmol), BINAP (6.4 mg, 0.0102 mmol), cesium carbonate (20.0 mg, 0.0615 mmol) and THF (0.8 mL) were mixed and stirred at room temperature for 1-3 minutes. To the resulting mixture was added 5-(6-chloro-2-morpholin-4-yl-pyrimidin-4-yl)-pyridin-2-ylamine (12.0 mg, 0.041 mmol) followed by 6-methoxypyridin-3-ylamine (10.2 mg, 0.082 mmol). The glass pressure vessel was sealed and stirred at 95° C. for 90 minutes. The reaction mixture was filtered and concentrated under reduced pressure. The product was purified by preparative reverse phase HPLC to give [6-(6-amino-pyridin-3-yl)-2-morpholin-4-yl-pyrimidin-4-yl]-(6-methoxy-pyridin-3-yl)-amine (5.0 mg, 32%). LC/MS (m/z): 380.1 (MH+), Rt 1.82 minutes.

후처리

  1. customThe glass pressure vessel was sealed
  2. stirringstirred at 95° C. for 90 minutes
  3. filtrationThe reaction mixture was filtered
  4. concentrationconcentrated under reduced pressure
  5. customThe product was purified by preparative reverse phase HPLC

출처 및 근거

ORD 기록
ord-a27ccd6a967243999146233a52b1fc90
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08217035B2

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