Ethynyltributyltin → 2-[(S)-1-phenylethylamino]-4-[6-(4-tributylstannyl-triazol-1-yl)benzimidazol-1-yl]pyrimidine

HRID 2300817Notes

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]=[C:22]([N:25]=[N+:26]=[N-:27])[CH:23]=[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]([Sn:32]([CH2:39][CH2:40][CH2:41][CH3:42])([CH2:35][CH2:36][CH2:37][CH3:38])[C:33]#[CH:34])[CH2:29][CH2:30][CH3:31]>O1CCOCC1>[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[C:22]([N:25]5[CH:34]=[C:33]([Sn:32]([CH2:28][CH2:29][CH2:30][CH3:31])([CH2:39][CH2:40][CH2:41][CH3:42])[CH2:35][CH2:36][CH2:37][CH3:38])[N:27]=[N:26]5)[CH:23]=[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: 100 °C

Procedure

A solution containing 95 mg of 2-[(S)-1-phenylethylamino]-4-[6-azidobenzimidazol-1-yl]pyrimidine and 386 μL tributyl-ethynylstannane in 2 mL 1,4-dioxane was stirred at 100° C. for 48 hours under 1 atm of nitrogen. The solution was concentrated under reduced pressure. The residue was purified by flash chromatography eluting with methanol in methylene chloride to give 139 mg of the title compound. RF: 0.4 (5% MeOH in CH2Cl2). 1H NMR (500 MHz, CD3OD): δ0.91 (t, J=7.4 Hz, 3H), 1.25 (t, J=8.1 Hz, 2H), 1.39 (m, 2H), 1.57 (d, J=6.9 Hz, 3H), 1.65 (m, 2H), 5.22 (q, J=7.1 Hz, 1H), 7.03 (d, J=5.5 Hz, 1H), 7.0-7.4 (m, 5H), 7.76 (m, 1H), 7.85 (d, J=8.7 Hz, 1H), 8.35 (d, J=5.3 Hz, 1H), 8.50 (s, 1H), 8.91 (m, 2H). Mass Spectrum (CH3CN-TFA-NH4HCO2-ESI): 673.2 (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-89e06f375306481395f39a9403d0ce94
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06498165B1

Reaction notes

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