Sodium Carbonate → HCID 66927369, compound

HRID 1484981Notes

Reaction equation

Br[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:13]=[C:12]([C:14]([CH3:17])([CH3:16])[CH3:15])[NH:11][N:10]=2)[C:5]([Cl:18])=[CH:4][N:3]=1.[C:19]([NH:23][S:24]([C:27]1[S:28][C:29](B2OC(C)(C)C(C)(C)O2)=[CH:30][CH:31]=1)(=[O:26])=[O:25])([CH3:22])([CH3:21])[CH3:20].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1>[C:19]([NH:23][S:24]([C:27]1[S:28][C:29]([C:2]2[N:7]=[C:6]([NH:8][C:9]3[CH:13]=[C:12]([C:14]([CH3:17])([CH3:16])[CH3:15])[NH:11][N:10]=3)[C:5]([Cl:18])=[CH:4][N:3]=2)=[CH:30][CH:31]=1)(=[O:25])=[O:26])([CH3:22])([CH3:20])[CH3:21]

Participants

Conditions

Temperature: 95 °C

Procedure

A mixture of 2-bromo-N-(5-tert-butyl-1H-pyrazol-3-yl)-5-chloropyrimidin-4-amine (250 mg, 0.87 mmol), PdCl2(dppf)CH2Cl2 (106 mg, 0.13 mmol, 0.15 eq), N-tert-butyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-sulfonamide (336 mg, 1.13 mmol, 1.3 eq), Na2CO3 (323 mg, 3.18 mmol, 3.5 equiv.) in dioxane was heated at 95° C. for 2 h under N. The reaction mixture was cooled to room temperature, and extracted with THF. The combined layers were concentrated and purified by silica gel chromatography (EA/PE 1:2) to afford N-tert-butyl-5-(4-(5-tert-butyl-1H-pyrazol-3-ylamino)-5-chloropyrimidin-2-yl)thiophene-2-sulfonamide (95 mg, 21%). LC-MS (m/z)=427 [M+H]+

Workup

temperatureThe reaction mixture was cooled to room temperature
extractionextracted with THF
concentrationThe combined layers were concentrated
custompurified by silica gel chromatography (EA/PE 1:2)

Sources & evidence

ORD record: ord-1726a8683a9d4b5788fbb45cd1a7f129
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422271B2

Reaction notes

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