Dibutyltin oxide → HCID 178525387, compound

HRID 870601Notes

Reaction equation

[N:1]([Si](C)(C)C)=[N+:2]=[N-:3].C([Sn](CCCC)=O)CCC.[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:39][CH2:40][CH2:41][CH2:42][C:43]#[N:44])=[O:38])[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:39][CH2:40][CH2:41][CH2:42][C:43]3[NH:44][N:3]=[N:2][N:1]=3)=[O:38])[CH2:34][C:32]=2[N:33]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Add azidotrimethylsilane (3.5 mL; 9.7 equiv; 26.27 mmoles) and dibutyloxostannane (0.163 g; 0.25 equiv; 0.66 mmoles) to a solution of 3-cyanopropyl 2-(indan-2-ylamino)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylate (0.98 g; 1.0 equiv; 2.70 mmoles) in toluene (20.4 mL). Heat the reaction mixture to 100° C. for 18 hours. Concentrate the solution and purify by reverse phase chromatography followed by silica gel chromatography (0 to 15% methanol in chloroform) to afford the desired 3-(1H-tetrazol-5-yl)propyl 2-(2,3-dihydro-1H-inden-2-ylamino)-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidine-6-carboxylate (0.097 g; 9%) as a brown solid: MS (m/z): 407(M+1).

Workup

concentrationConcentrate the solution
custompurify by reverse phase chromatography

Sources & evidence

ORD record: ord-5a3ed6228c034535847183643b551d00
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969555B2

Reaction notes

Loading…