Potassium Carbonate → HCID 178434537, compound

HRID 1853048Notes

Reaction equation

[NH:1]1[CH:5]=[C:4]([C:6]2[N:11]3[CH:12]=[CH:13][N:14]=[C:10]3[CH:9]=[C:8]([C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)=[CH:17][CH:16]=3)[N:7]=2)[CH:3]=[N:2]1.[CH3:27]C1NN=CC=1B1OC(C)(C)C(C)(C)O1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:27][C:5]1[C:4]([C:6]2[N:11]3[CH:12]=[CH:13][N:14]=[C:10]3[CH:9]=[C:8]([C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)=[CH:17][CH:16]=3)[N:7]=2)=[CH:3][NH:2][N:1]=1

Participants

Conditions

Temperature: 100 °C

Procedure

4-(4-(5-Chloroimidazo[1,2-c]pyrimidin-7-yl)phenyl) morpholine (Example 113, Step D) (0.120 g, 0.381 mmol), 5-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.119 g, 0.572 mmol) and potassium carbonate (0.158 g, 1.144 mmol) were suspended in a mixture of DME (5 mL) and water (2 mL) and de-gassed with Ar(g). Tetrakis(triphenylphosphine)palladium (0) (0.0220 g, 0.0191 mmol) was added and the reaction sealed and heated at 100° C. for 4 hours. The reaction mixture was diluted with water and filtered. The solids were washed with acetone and dried under high vacuum to afford 4-(4-(5-(3-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-7-yl)phenyl)morpholine (0.0660 g, 0.1831 mmol, 48.0% yield). MS (apci) m/z=361.1 (M+H).

Workup

customde-gassed with Ar(g)
customthe reaction sealed
filtrationfiltered
washThe solids were washed with acetone
customdried under high vacuum

Sources & evidence

ORD record: ord-23fc0786d2d943c59a65b32ffd1d8da2
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962596B2

Reaction notes

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