2-[(S)-1-Phenylethylamino]-4-[5-azidobenzimidazol-1-yl]pyrimidine → 2-[(S)-1-Phenylethylamino]-4-[5-(4-ethoxycarbonyltriazol-1-yl)benzimidazol-1-yl]pyrimidine

HRID 2300815Notes

Reaction equation

[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][C:23]([N:25]=[N+:26]=[N-:27])=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:28]([O:30][C:31](=[O:38])[CH:32]=[C:33](NC)NC)[CH3:29]>O1CCOCC1>[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][C:23]([N:25]5[CH:33]=[C:32]([C:31]([O:30][CH2:28][CH3:29])=[O:38])[N:27]=[N:26]5)=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A solution containing 12.5 mg of 2-[(S)-1-phenylethylamino]-4-[5-azidobenzimidazol-1-yl]pyrimidine and about 100 μL ethyl-3,3-dimethylaminoacrylate in 2 mL 1,4-dioxane was stirred at 90° C. for 48 hours. The solution was concentrated under reduced pressure. The residue was purified by flash chromatography eluting with methanol in methylene chloride to give 6.0 mg of the title compound. RF: 0.4 (5% MeOH in CH2Cl2). 1H NMR (500 MHz, 1:1 CD3OD/CDCl3): δ 1.42 (t, J=7.1 Hz, 3H), 1.59 (d, J=7.1 Hz, 3H), 4.44 (q, J=7.1 Hz, 2H), 5.16 (m, 1H), 6.92 (d, J=5.5 Hz, 1H), 7.24 (br s, J=7.3 Hz, 1H), 7.36 (br s, J=7.3 Hz, 2H), 7.45 (d, J=7.3 Hz, 2H), 7.68-7.8 (m, 1H), 7.95 (m, 1H), 8.14 (br s, 1H), 8.38 (br s, J=5.3 Hz, 1H), 8.77 (m, 1H), 8.92 (s, 1H). Mass Spectrum (CH3CN-TFA-NH4HCO2-ESI): 455.2 (M+1).

Workup

concentrationThe solution was concentrated under reduced pressure
customThe residue was purified by flash chromatography
washeluting with methanol in methylene chloride

Sources & evidence

ORD record: ord-a70ccf3d2b9a4274b1ba8bd0f47fe23c
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06498165B1

Reaction notes

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