Cesium carbonate → HCID 118390019, compound

HRID 1478061Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:23][CH:12]3[CH2:13][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH:11]3[CH2:10]2)[C:5]([Cl:24])=[CH:4][N:3]=1.Cl.[CH:26]1([C:29]2[NH:33][N:32]=[C:31]([NH2:34])[CH:30]=2)[CH2:28][CH2:27]1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:24][C:5]1[C:6]([NH:8][CH:9]2[CH2:23][CH:12]3[CH2:13][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH:11]3[CH2:10]2)=[N:7][C:2]([NH:34][C:31]2[CH:30]=[C:29]([CH:26]3[CH2:28][CH2:27]3)[NH:33][N:32]=2)=[N:3][CH:4]=1

Participants

Conditions

Temperature: 150 °C

Procedure

To a suspension of tert-butyl 5-[(2,5-dichloropyrimidin-4-yl)amino]-hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate (373.3 mg, 1.00 mmol) and 5-cyclopropyl-1H-pyrazol-3-amine hydrochloride (376.4 mg, 2.36 mmol) in dioxane (10 mL) were added Pd(OAc)2 (75.9 mg, 0.34 mmol), BINAP (164.0 mg, 0.25 mmol) and Cs2CO3 (1.08 g, 3.31 mmol). The reaction mixture was stirred at 150° C. under microwave radiation for 2 h and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=2/1) to give the title compound as a pale yellow solid (0.29 g, 63%).

Workup

concentrationconcentrated in vacuo
customThe residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=2/1)

Sources & evidence

ORD record: ord-fdc9b38781574620ab3d40854ab8eaf5
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403801B2

Reaction notes

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