Dibutyltin oxide → HCID 178520578, compound

HRID 870595Notes

Reaction equation

C([Sn](CCCC)=O)CCC.[N:11]([Si](C)(C)C)=[N+:12]=[N-:13].[CH2:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20][CH:19]1[NH:27][C:28]1[N:29]=[CH:30][C:31]2[CH2:36][N:35]([C:37](=[O:44])[CH2:38][CH2:39][CH2:40][CH2:41][C:42]#[N:43])[CH2:34][C:32]=2[N:33]=1>C1(C)C=CC=CC=1>[CH2:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20][CH:19]1[NH:27][C:28]1[N:29]=[CH:30][C:31]2[CH2:36][N:35]([C:37](=[O:44])[CH2:38][CH2:39][CH2:40][CH2:41][C:42]3[NH:43][N:13]=[N:12][N:11]=3)[CH2:34][C:32]=2[N:33]=1

Participants

Conditions

Temperature: 105 °C

Procedure

Add dibutyloxostannane (0.071 g; 1.33 equiv; 0.29 mmoles) and azidotrimethylsilane (1.6 mL; 56 equiv; 12.01 mmoles) to a stirred solution of 6-[2-(indan-2-ylamino)-5,7-dihydropyrrolo[3,4-d]pyrimidin-6-yl]-6-oxo-hexanenitrile (0.077 g; 1.0 equiv; 0.213 mmoles) in toluene (6 mL). Heat the resulting solution to 105° C. for 16 hours. Cool the reaction mixture to ambient temperature and concentrate. Dissolve the residue in methanol (5 mL) and load the solution on an SCX column (eluting with methanol to 7N ammonia in methanol) to afford the crude product, which is purified by reverse phase chromatography to give 1-[2-(2,3-dihydro-1H-inden-2-ylamino)-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidin-6-yl]-5-(1H-tetrazol-5-yl)pentan-1-one (0.0265 g; 31%): MS (m/z): 405(M+1).

Workup

temperatureCool the reaction mixture to ambient temperature
concentrationconcentrate
dissolutionDissolve the residue in methanol (5 mL)
washon an SCX column (eluting with methanol to 7N ammonia in methanol)
customto afford the crude product, which
customis purified by reverse phase chromatography

Sources & evidence

ORD record: ord-a1a831b35c514598a615cb35df17305d
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969555B2

Reaction notes

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