Water → HCID 58539067, compound

HRID 1804680Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:18]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[O:19])[CH:5]=[CH:6][C:7]=1[NH:8][C:9]1[N:14]=[C:13]([NH:15][CH3:16])[C:12]([Cl:17])=[CH:11][N:10]=1.[C:26]([O-])(=O)[CH3:27].[K+].[C:31](=O)([O-])[O-].[Na+].[Na+].C(#N)C.O>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:17][C:12]1[C:13]([NH:15][CH3:16])=[N:14][C:9]([NH:8][C:7]2[CH:6]=[CH:5][C:4]([C:18]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[O:19])=[CH:3][C:2]=2[CH:27]2[CH2:26][CH2:31]2)=[N:10][CH:11]=1

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of [3-Bromo-4-(5-chloro-4-methylamino-pyrimidin-2-ylamino)-phenyl]-morpholin-4-yl-methanone (0.0500 g, 0.117 mmol), potassium acetate (0.0172 g, 0.176 mmol), sodium carbonate (0.0186 g, 0.176 mmol) and 1,1′-bis(diphenylphosphino)ferrocenepalladium (II) chloride (0.00478 g, 0.00585 mmol) were weighed into a microwave vial equipped with a stir bar. Acetonitrile (0.94 mL, 18 mmol) and degassed Water (0.3 mL, 20 mmol) were then added and the reaction mixture was degassed with nitrogen for 4 mins and then heated to 140° C. under microwave irradiation for 80 min. The mixture was then filtered through celite, eluting with ethyl acetate and concentrated in vacuo. Purification of the crude product was achieved by reverse phase HPLC.

Workup

customvial equipped with a stir bar
additionwere then added
customthe reaction mixture was degassed with nitrogen for 4 mins
filtrationThe mixture was then filtered through celite
washeluting with ethyl acetate
concentrationconcentrated in vacuo
customPurification of the crude product

Sources & evidence

ORD record: ord-039f20099d304552ba228e9a4285aeaf
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354420B2

Reaction notes

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