Cesium carbonate → HCID 59507926, compound

HRID 1043808Notes

Reaction equation

HRID 1043808 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]=[N:68][C:69]([NH2:72])=[N:70][CH:71]=2)[CH:55]=1.[CH3:73][O:74][C:75]1[CH:84]=[CH:83][CH:82]=[C:81]2[C:76]=1[CH:77]=[C:78]([NH2:85])[CH:79]=[N:80]2>CC([O-])=O.CC([O-])=O.[Pd+2].C1COCC1>[NH2:72][C:69]1[N:68]=[CH:67][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:85][C:78]3[CH:79]=[N:80][C:81]4[C:76]([CH:77]=3)=[C:75]([O:74][CH3:73])[CH:84]=[CH:83][CH:82]=4)[CH:55]=2)=[CH:71][N:70]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 59507478HCID 59507478, compoundHCID 595077435-Methoxyquinolin-3-amine

Product 1

HCID 59507926HCID 59507926, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
110 °C

Procedure

The desired compound was prepared as described in Example 2: Pd(OAc)2, BINAP, cesium carbonate, THF (0.8 mL) were mixed with 5-(6-chloro-2-morpholinopyrimidin-4-yl)pyrimidin-2-amine (1 eq.) and 5-methoxyquinolin-3-amine (2 eq), which was prepared as shown in Method 20. The mixture was heated under microwave irradiation for 10 minutes at 110° C. The solution was filtered and concentrated Under reduced pressure. The crude product was purified by preparative reverse phase HPLC. LC/MS (m/z): 431.2 (MH+), Rt 2.03 minutes.

Workup

  1. customwas prepared
  2. filtrationThe solution was filtered
  3. concentrationconcentrated Under reduced pressure
  4. customThe crude product was purified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-dfa34069afd946d2863c7c00b0ea2782
Source dataset
uspto-grants-2013_10
Patent number
US08563549B2

Reaction notes

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