Cesium carbonate → 2-(2-(2-(5-Chloro-2-(6-methylpyridin-3-ylamino)pyrimidin-4-yl)ethyl)phenyl)propanamide

HRID 592422Notes

Reaction equation

[Cl:1][C:2]1[C:3]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH:23]([CH3:27])[C:24]([NH2:26])=[O:25])=[N:4][C:5](NC2C=NN(C)C=2)=[N:6][CH:7]=1.[NH2:28][C:29]1[CH:30]=[CH:31][C:32]([CH3:35])=[N:33][CH:34]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:1][C:2]1[C:3]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH:23]([CH3:27])[C:24]([NH2:26])=[O:25])=[N:4][C:5]([NH:28][C:29]2[CH:34]=[N:33][C:32]([CH3:35])=[CH:31][CH:30]=2)=[N:6][CH:7]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 2-(2-(2-(5-chloro-2-(1-methyl-1H-pyrazol-4-ylamino)pyrimidin-4-yl)ethyl)phenyl)propanamide WAK-011-06-05 (0.080 g, 0.25 mmol), 5-amino-2-methylpyridine (0.053 g, 0.49 mmol), Xantphos (0.0057 g, 0.010 mmol) and Cs2CO3 (0.24 g, 0.74 mmol) in 1,4-dioxane (3 mL) was bubbled with nitrogen for 10 minutes. Palladium (II) acetate (0.0011 g, 0.0049 mmol) was added and the mixture was heated at 120° C. under microwave irradiation for 20 minutes. The volatiles were removed in vacuo and the residue was purified by silica gel column chromatography (Combiflash Rf, 0-10% MeOH in DCM) to give the title compound 41 as a light yellow solid (0.032 g, 33%). LCMS-C: rt 4.24 min; m/z 396 [M+H]+.

Workup

customThe volatiles were removed in vacuo
customthe residue was purified by silica gel column chromatography (Combiflash Rf, 0-10% MeOH in DCM)

Sources & evidence

ORD record: ord-329a3f8fbf73472b8dd91d863ec5cc18
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238644B2

Reaction notes

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