Piperidine → 5-Bromo-7-(phenylsulfonyl)-4-(piperidin-1-yl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 2180968Notes

Reaction equation

[C:1]1([S:7]([N:10]2[C:14]3[N:15]=[CH:16][N:17]=[C:18](Cl)[C:13]=3[C:12]([Br:20])=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1>C(O)(C)(C)C>[C:1]1([S:7]([N:10]2[C:14]3[N:15]=[CH:16][N:17]=[C:18]([N:21]4[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]4)[C:13]=3[C:12]([Br:20])=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 2.0 g (5.37 mmol) of the product from Method U and 1.1 g (13.4 mmol) of piperidine in 10 mL of tert-butanol was heated with stirring at 60° C. for 2 h. After cooling to room temperature, the reaction mixture was partitioned between dichloromethane (25 mL) and water (25 mL). The dichloromethane layer was dried over sodium sulfate (Na2SO4) and concentrated to dryness in vacuo affording 2.2 g (97%) of the title compound. 1H NMR (400 MHz) (CDCl3) δ: 1.63-1.72 (m, 6H), 3.54-3.57 (m, 4H), 7.53 (t, 2H, J=2.0 Hz), 7.60 (s, 1H), 7.61 (t, 1H, J=2.0 Hz), 8.17-8.20 (m, 2H), 8.43 (s, 1H). LRMS: 422.7, 420.7 (M+1).

Workup

temperaturewas heated
temperatureAfter cooling to room temperature
customthe reaction mixture was partitioned between dichloromethane (25 mL) and water (25 mL)
dry with materialThe dichloromethane layer was dried over sodium sulfate (Na2SO4)
concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record: ord-3c3d49870ac143c7ab654f5b439d502f
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06890929B2

Reaction notes

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