1,8-Diazabicyclo(5.4.0)undec-7-ene → 4-chloro-7-(3,3-difluorocyclobutyl)-2-(methylsulfanyl)-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine

HRID 1775471Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-{4-chloro-6-[(3,3-difluorocyclobutyl)amino]-2-(methylsulfanyl)pyrimidin-5-yl}ethyl methanesulfonate (922 mg, 2.38 mmol) in DMF (23 mL) was added DBU (0.725 mL, 4.75 mmol). The mixture was stirred at 80° C. for 1 h, whereupon the reaction mixture was diluted with EtOAc (40 mL), washed with water (20 mL) and brine (20 mL), dried over Na2SO4 and concentrated under reduced pressure to give 649 mg (94%) of the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 4.44-4.33 (m, 1 H), 3.75 (t, J=8.5 Hz, 2 H), 3.13-2.99 (m, 2 H), 2.98-2.92 (m, 2 H), 2.91-2.81 (m, 2 H), 2.42 (s, 3 H). m/z (APCI+) for C11H12ClF2N3S 292.0 (M+H)+.

Workup

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

Sources & evidence

ORD record: ord-1f7efdd6ff614de79debe6ee89763320
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260439B2

Reaction notes

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