Cesium carbonate → HCID 58539090, compound

HRID 1804677Notes

Reaction equation

Br[C:2]1[C:3]([NH:25][CH3:26])=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[O:16])=[CH:11][C:10]=2[O:23][CH3:24])=[N:6][CH:7]=1.[CH:27]1([B-](F)(F)F)[CH2:30][CH2:29][CH2:28]1.[K+].C(=O)([O-])[O-].[Cs+].[Cs+].C12(P(C34CC5CC(CC(C5)C3)C4)CCCC)CC3CC(CC(C3)C1)C2>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C1(C)C=CC=CC=1>[CH:27]1([C:2]2[C:3]([NH:25][CH3:26])=[N:4][C:5]([NH:8][C:9]3[CH:14]=[CH:13][C:12]([C:15]([N:17]4[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)=[O:16])=[CH:11][C:10]=3[O:23][CH3:24])=[N:6][CH:7]=2)[CH2:30][CH2:29][CH2:28]1

Participants

Conditions

Temperature: 11 °C

Procedure

To a microwave tube was added (4-(5-bromo-4-(methylamino)pyrimidin-2-ylamino)-3-methoxyphenyl)(morpholino)methanone (100 mg, 0.24 mmol), potassium cyclobutyltrifluoroborate (177 mg, 1.1 mmol), cesium carbonate (0.23 g, 0.71 mmol), toluene (2.9 mL) and water (0.3 mL). The mixture was degassed by nitrogen bubbling for 15 mintues. di-(1-admantyl)-n-butylphosphine (19 mg, 0.053 mmol) and palladium acetate (2.6 mg, 0.026 mmol) was then added. The reaction was sealed and heated at 11° C. for 2 hours. The reaction mixture was filtered and concentrated. The crude product was purified by RP-HPLC to give the desire product (8.1 mg, 8.6%).

Workup

customThe mixture was degassed by nitrogen bubbling for 15 mintues
customThe reaction was sealed
filtrationThe reaction mixture was filtered
concentrationconcentrated
customThe crude product was purified by RP-HPLC

Sources & evidence

ORD record: ord-1368914b953d470f8eda176aa1af8c74
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354420B2

Reaction notes

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