Cesium carbonate → [6-(6-Amino-pyridin-3-yl)-2-morpholin-4-yl-pyrimidin-4-yl]-(6-methoxy-pyridin-3-yl)-amine
Reaction equation
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]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
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.
Workup
- customThe glass pressure vessel was sealed
- stirringstirred at 95° C. for 90 minutes
- filtrationThe reaction mixture was filtered
- concentrationconcentrated under reduced pressure
- customThe product was purified by preparative reverse phase HPLC
Sources & evidence
- ORD record
- ord-a27ccd6a967243999146233a52b1fc90
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08217035B2
Reaction notes
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