Tetrahydrofuran → ethyl 4-(3-(3-(cyanomethyl)ureido)phenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate

HRID 882134Notes

Reaction equation

[C:1]([CH2:3][NH:4][C:5](=[O:35])[NH:6][C:7]1[CH:8]=[C:9]([C:13]2[C:14]3[C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:20][N:19](COCC[Si](C)(C)C)[C:15]=3[N:16]=[CH:17][N:18]=2)[CH:10]=[CH:11][CH:12]=1)#[N:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1>C(OCC)(=O)C>[C:1]([CH2:3][NH:4][C:5](=[O:35])[NH:6][C:7]1[CH:8]=[C:9]([C:13]2[C:14]3[C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:20][NH:19][C:15]=3[N:16]=[CH:17][N:18]=2)[CH:10]=[CH:11][CH:12]=1)#[N:2]

Participants

Conditions

Temperature: 45 °C

Procedure

Ethyl 4-(3-(3-(cyanomethyl)ureido)phenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (65.4 mg, 0.132 mmol) was mixed with 1 M TBAF in THF (2.64 mL, 2.64 mmol) and heated at 45° C. for 1 hour. The reaction mixture was diluted with ethyl acetate (5 mL) and washed with water (5 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica eluting with 0-20% MeOH/DCM to give ethyl 4-(3-(3-(cyanomethyl)ureido)phenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate. LRMS (EST) calc'd for C18H17N6O3 [M+H]+: 365, found 365. 1H NMR (600 MHz, DMSO-D6) δ 12.96 (bs, 1H), 9.08 (s, 1H), 8.89 (s, 1H), 8.29 (s, 1H), 7.76 (s, 1H), 7.54 (d, J=8.21 Hz, 1H), 7.35 (t, J=7.63 Hz, 1H), 7.20 (d, J=7.63 Hz, 1H), 6.71 (d, J=5.28 Hz, 1H), 4.13 (d, J=5.87 Hz, 2H), 3.86 (q, J=6.8 Hz, 2H), 0.84 (t, J=7.04 Hz, 3H).

Workup

washwashed with water (5 mL)
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by chromatography on silica eluting with 0-20% MeOH/DCM

Sources & evidence

ORD record: ord-8c2abf72cd5e42a28e76a7a9d5894ee3
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08993756B2

Reaction notes

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