Dimethylformamide → HCID 178521436, compound

HRID 870571Notes

Reaction equation

CN(C)C=O.[CH2:6]([O:10][CH2:11][C:12]([N:14]1[CH2:22][C:21]2[CH:20]=[N:19][C:18]([NH:23][CH:24]3[CH2:32][C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH2:25]3)=[N:17][C:16]=2[CH2:15]1)=[O:13])[CH2:7][C:8]#[CH:9].[Na].O=C1O[C@H]([C@H](CO)O)C(O)=C1O.[N:46]([Si](C)(C)C)=[N+:47]=[N-:48]>O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2].O>[CH2:25]1[C:26]2[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:32][CH:24]1[NH:23][C:18]1[N:19]=[CH:20][C:21]2[CH2:22][N:14]([C:12](=[O:13])[CH2:11][O:10][CH2:6][CH2:7][C:8]3[N:46]=[N:47][NH:48][CH:9]=3)[CH2:15][C:16]=2[N:17]=1

Participants

Conditions

Temperature: 23 °C

Procedure

Add dimethylformamide (27 mL) and water (27 mL) to a flask containing 2-(but-3-yn-1-yloxy)-1-[2-(2,3-dihydro-1H-inden-2-ylamino)-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidin-6-yl]ethanone (2.90 g, 8.00 mmol). Add copper (II) sulfate pentahydrate (400 mg, 1.60 mmol) and L-ascorbic acid sodium salt (3.17 g, 16.0 mmol). Evacuate flask and backfill with nitrogen (×2), then add azidotrimethylsilane (7.37 g, 8.53 mL, 64.0 mmol) and heat the reaction to 90° C. for 70 minutes. Cool the reaction mixture to 23° C. and remove all solvent in vacuo. Suspend the residue in methanol/dichloromethane and then add silica gel and remove solvent in vacuo. Load this material onto a loading column and purify via silica gel column chromatography (gradient elution: 0-9% methanol in ethyl acetate) to give the title compound (980 mg, 30%). MS (m/z): 406(M+1).

Workup

customEvacuate flask
customthe reaction to 90° C. for 70 minutes
customremove all solvent in vacuo
customadd silica gel and remove solvent in vacuo
customLoad this material onto a loading column and purify via silica gel column chromatography (gradient elution: 0-9% methanol in ethyl acetate)

Sources & evidence

ORD record: ord-d21f45cf500f470499f214792ab6fbb6
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969555B2

Reaction notes

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