Cesium carbonate → HCID 67981041, compound

HRID 1408868Notes

Reaction equation

[C:1]([C:4]12[CH2:11][C:8]([NH:12][C:13](=[O:22])[O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)([CH2:9][CH2:10]1)[CH2:7][CH2:6][CH2:5]2)(=[O:3])[NH2:2].C([O-])([O-])=O.[Cs+].[Cs+].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:76]1[CH:81]=[CH:80][N:79]=[C:78]([CH3:82])[N:77]=1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:82][C:78]1[N:79]=[C:80]([NH:2][C:1]([C:4]23[CH2:11][C:8]([NH:12][C:13](=[O:22])[O:14][CH2:15][C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)([CH2:9][CH2:10]2)[CH2:7][CH2:6][CH2:5]3)=[O:3])[CH:81]=[CH:76][N:77]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of benzyl 5-carbamoylbicyclo[3.2.1]octan-1-ylcarbamate (1 g, 3.3 mmol) and Cs2CO3 (1.6 g, 4.9 mmol) and BINAP (200 mg, 0.3 mmol) in toluene (60 mL), was added 4-chloro-2-methylpyrimidine (430 mg, 3.3 mmol), followed by Pd2(dba)3 (300 mg, 0.32 mmol). The mixture was stirred at 100° C. under N2 overnight. After cooled to room temperature, the reaction mixture was concentrated under reduced pressure and the resulting residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate: 4/1) to give 1 g (77%) of benzyl 5-(2-methylpyrimidin-4-ylcarbamoyl)bicyclo[3.2.1]octan-1-ylcarbamate as a light yellow oil. ESI-MS m/z: 395 (M+H)+.

Workup

temperatureAfter cooled to room temperature
concentrationthe reaction mixture was concentrated under reduced pressure
customthe resulting residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate: 4/1)

Sources & evidence

ORD record: ord-807a39402ecb4735b585c49c1269228a
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921370B2

Reaction notes

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