1,8-Diazabicyclo(5.4.0)undec-7-ene → tert-butyl(3S)-3-[4-chloro-2-(methylsulfanyl)-5,6-dihydro-7H-pyrrolo[2,3-d]pyrimidin-7-yl]-3-methylpyrrolidine-1-carboxylate

HRID 1775492Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([S:8][CH3:9])[N:5]=[C:4]([NH:10][C@@:11]2([CH3:23])[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12]2)[C:3]=1[CH2:24][CH2:25]OS(C)(=O)=O.C1CCN2C(=NCCC2)CC1>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[C:3]2[CH2:24][CH2:25][N:10]([C@@:11]3([CH3:23])[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])[CH2:12]3)[C:4]=2[N:5]=[C:6]([S:8][CH3:9])[N:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of tert-butyl(3S)-3-{[6-chloro-2-(methylsulfanyl)-5-{2-[(methylsulfonyl)oxy]ethyl}pyrimidin-4-yl]amino}-3-methylpyrrolidine-1-carboxylate (1635 mg, 3.4 mmol) in DMF (34 mL) was added DBU (1.1 mL, 6.8 mmol) and the mixture was stirred at 80° C. for 90 min. The reaction mixture was diluted with EtOAc (20 mL), washed with water (20 mL) and brine (20 mL), dried over Na2SO4 and concentrated to give the title compound (1.24 g, 95%) as a light yellow-white solid. 1H NMR (400 MHz, DMSO-d6) δ 3.80-3.57 (m, 4 H), 3.40-3.35 (m, 1 H), 3.28-3.19 (m, 1 H), 2.91 (t, J=8.9 Hz, 2 H), 2.42 (s, 3 H), 2.39-2.24 (m, 1 H), 2.07-1.94 (m, 1 H), 1.39 (d, J=5.4 Hz, 9 H), 1.28 (s, 3 H). m/z (APCI+) for C17H25ClN4O2S 385.1 (M+H)+.

Workup

washwashed with water (20 mL) and brine (20 mL)
dry with materialdried over Na2SO4
concentrationconcentrated

Sources & evidence

ORD record: ord-cc961971c81941ae90fa1fbd9ed16410
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260439B2

Reaction notes

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