Cesium carbonate → 3-Methyl-4-(3-(pyrimidin-4-yl)pyridin-2-yloxy)benzenamine

HRID 446279Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH3:9])[CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].Cl[C:17]1[C:22]([C:23]2[CH:28]=[CH:27][N:26]=[CH:25][N:24]=2)=[CH:21][CH:20]=[CH:19][N:18]=1>CN1C(=O)CCC1>[CH3:9][C:4]1[CH:3]=[C:2]([NH2:1])[CH:7]=[CH:6][C:5]=1[O:8][C:17]1[C:22]([C:23]2[CH:28]=[CH:27][N:26]=[CH:25][N:24]=2)=[CH:21][CH:20]=[CH:19][N:18]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To 4-amino-2-methyl-phenol (193 mg, 1.57 mmol) was added Cs2CO3 (1.02 g, 3.14 mmol) and NMP (2.0 mL). The mixture was heated for 5 minutes at 100° C., cooled to RT and 4-(2-chloro-pyridin-3-yl)-pyrimidine (300 mg, 1.57 mmol) was added. The mixture was heated in the microwave to 210° C. for 20 minutes, cooled, filtered through a plug of cotton and purified by reverse-phase HPLC (Gilson, acidic mobile phase) to yield 3-methyl-4-(3-pyrimidin-4-yl-pyridin-2-yloxy)-phenylamine. MS m/z=279 [M+1]+. Calc'd for C16H14N4O: 278.32.

Workup

temperaturecooled to RT
temperatureThe mixture was heated in the microwave to 210° C. for 20 minutes
temperaturecooled
filtrationfiltered through a plug of cotton
custompurified by reverse-phase HPLC (Gilson, acidic mobile phase)

Sources & evidence

ORD record: ord-d6f8c597a9ed4cfbb55b2d5df95461e3
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08476434B2

Reaction notes

Loading…