Sodium Carbonate → N-tert-butyl-5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-2-yl)thiophene-2-sulfonamide

HRID 1484877Notes

Reaction equation

Br[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:13]=[C:12]([CH:14]3[CH2:16][CH2:15]3)[NH:11][N:10]=2)[CH:5]=[CH:4][N:3]=1.[C:17]([NH:21][S:22]([C:25]1[S:26][C:27](B2OC(C)(C)C(C)(C)O2)=[CH:28][CH:29]=1)(=[O:24])=[O:23])([CH3:20])([CH3:19])[CH3:18].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.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]>[C:17]([NH:21][S:22]([C:25]1[S:26][C:27]([C:2]2[N:7]=[C:6]([NH:8][C:9]3[CH:13]=[C:12]([CH:14]4[CH2:16][CH2:15]4)[NH:11][N:10]=3)[CH:5]=[CH:4][N:3]=2)=[CH:28][CH:29]=1)(=[O:23])=[O:24])([CH3:20])([CH3:18])[CH3:19]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-bromo-N-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidin-4-amine (300 mg, 1.071 mmol, 1.0 eq), N-tert-butyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-sulfonamide (443.7 mg, 1.285 mmol, 1.2 eq), Pd(dppf)Cl2 (87.5 mg, 0.1071 mmol, 0.1 eq), Na2CO3 (454.1 mg, 4.284 mmol, 4 eq) in 1,4-dioxane (20 ml) and water (4 ml) was stirred at 100° C. under a nitrogen atmosphere for 15 h. The reaction mixture was allowed to cool to room temperature and concentrated to give a residue, which was purified by silica gel chromatography (CH2Cl2/methanol 500:1 to 50:1 as eluent) to afford N-tert-butyl-5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-2-yl)thiophene-2-sulfonamide (300 mg, 66.9%) as a solid. LC-MS (m/z)=419.1 [M+H]+.

Workup

temperatureto cool to room temperature
concentrationconcentrated
customto give a residue, which
customwas purified by silica gel chromatography (CH2Cl2/methanol 500:1 to 50:1 as eluent)

Sources & evidence

ORD record: ord-a8e0e9dd5ca944a4a4f1c9d6b7a9d53c
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422271B2

Reaction notes

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