Cesium carbonate → HCID 54756379, compound

HRID 1804676Notes

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)[CH2:29][CH2:28]1.[K+].C(=O)([O-])[O-].[Cs+].[Cs+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>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)[CH2:29][CH2:28]1

Participants

Conditions

Temperature: 140 °C

Procedure

To a microwave tube was added (4-(5-bromo-4-(methylamino)pyrimidin-2-ylamino)-3-methoxyphenyl)(morpholino)methanone (56 mg, 0.13 mmol), potassium cyclopropyltrifluoroborate (39 mg, 0.27 mmol), cesium carbonate (0.13 g, 0.40 mmol), toluene (1.8 mL) and water (0.2 mL). The mixture was degassed by nitrogen bubbling for 15 mintues. XPhos (6.4 mg, 0.013 mmol) and palladium acetate (2 mg, 0.01 mmol) was then added. The reaction was heated in a Biotage microwave at 140° C. for 20 minutes. The reaction mixture was filtered and concentrated. The crude product was purified by RP-HPLC to give the desire product (12.6 mg, 25%).

Workup

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

Sources & evidence

ORD record: ord-c5e5558f031c43eba6b0e3401a9e0a1f
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354420B2

Reaction notes

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