Potassium Carbonate → 4-methyl-N3-(3-pyrimidin-4-yl-pyridin-2-yl)-benzene-1,3-diamine
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.Cl[C:48]1[C:53]([C:54]2[CH:59]=[CH:58][N:57]=[CH:56][N:55]=2)=[CH:52][CH:51]=[CH:50][N:49]=1.[C:60]([O:64][C:65](=[O:75])[NH:66][C:67]1[CH:72]=[CH:71][C:70]([CH3:73])=[C:69]([NH2:74])[CH:68]=1)([CH3:63])([CH3:62])[CH3:61].C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:73][C:70]1[CH:71]=[CH:72][C:67]([NH2:66])=[CH:68][C:69]=1[NH:74][C:48]1[C:53]([C:54]2[CH:59]=[CH:58][N:57]=[CH:56][N:55]=2)=[CH:52][CH:51]=[CH:50][N:49]=1.[C:60]([O:64][C:65](=[O:75])[NH:66][C:67]1[CH:72]=[CH:71][C:70]([CH3:73])=[C:69]([NH:74][C:48]2[C:53]([C:54]3[CH:59]=[CH:58][N:57]=[CH:56][N:55]=3)=[CH:52][CH:51]=[CH:50][N:49]=2)[CH:68]=1)([CH3:63])([CH3:61])[CH3:62]Participants
8
Reactant 4
Product 2
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 130 °C
Procedure
The title compound was prepared according to the procedure described in Tetrahedron 2001, 51, 7027-7034. Pd(OAc)2 (47 mg, 0.21 mmol), and rac-BINAP (131 mg, 0.21 mmol) were stirred in toluene (12 mL) at RT for 12 minutes. This mixture was added to 4-(2-chloro-pyridin-3-yl)-pyrimidine (1.01 g, 5.24 mmol), (3-amino-4-methyl-phenyl)-carbamic acid tert-butyl ester (1.63 g, 7.34 mmol), and K2CO3 (14.5 g, 105 mmol) in toluene (40 mL). The mixture was heated overnight at 130° C. in a sealed tube. The cooled reaction was filtered through a pad of Celite, partially concentrated and the resulting solid was filtered to yield [4-methyl-3-(3-pyrimidin-4-yl-pyridin-2-ylamino)-phenyl]-carbamic acid tert-butyl ester.
Workup
- customThe cooled reaction
- filtrationwas filtered through a pad of Celite
- concentrationpartially concentrated
- filtrationthe resulting solid was filtered
Sources & evidence
- ORD record
- ord-fca376be05a349bfb7cc06a04c26b84c
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08476434B2
Reaction notes
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