Azidotrimethylsilane → HCID 178523291, compound

HRID 870603Notes

Reaction equation

HRID 870603 reaction equation
[Na].O=C1O[C@H]([C@H](CO)O)C(O)=C1O.[CH2:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH:15]1[NH:23][C:24]1[N:25]=[CH:26][C:27]2[CH2:32][N:31]([C:33]([NH:35][CH2:36][CH2:37][CH2:38][C:39]#[CH:40])=[O:34])[CH2:30][C:28]=2[N:29]=1.[N:41]([Si](C)(C)C)=[N+:42]=[N-:43]>CN(C)C=O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[CH2:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH:15]1[NH:23][C:24]1[N:25]=[CH:26][C:27]2[CH2:32][N:31]([C:33]([NH:35][CH2:36][CH2:37][CH2:38][C:39]3[N:41]=[N:42][NH:43][CH:40]=3)=[O:34])[CH2:30][C:28]=2[N:29]=1

Participants

7

Reactant 3

HCID 78378AzidotrimethylsilaneHCID 66586226sodium L-ascorbic acidHCID 86726570HCID 86726570, compound

Product 1

HCID 178523291HCID 178523291, compoundYield 21.4%

Reagents, catalysts & solvents 3

HCID 24463Copper sulfate pentahydrateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Add copper(II)sulfate pentahydrate (0.049 g; 0.2 equiv; 0.20 mmoles) and L-ascorbic acid sodium salt (0.388 g; 2.0 equiv; 1.96 mmoles) to a deoxygenated solution of 2-(2,3-dihydro-1H-inden-2-ylamino)-N-(pent-4-yn-1-yl)-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidine-6-carboxamide (0.354 g; 1.0 equiv; 0.98 mmoles) in dimethylformamide (3.26 mL) and water (3.26 mL). Add azidotrimethylsilane (1.04 mL; 8 equiv; 7.84 mmoles) and heat the mixture to 90° C. for 1 hour, the cool to ambient temperature and stir for 16 hours. Concentrate the solution to dryness, and purify the resulting orange semisolid by column chromatography (0 to 10% methanol in ethyl acetate) to afford 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-(1H-1,2,3-triazol-4-yl)propyl]-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidine-6-carboxamide (0.085 g; 21%) as a solid: MS (m/z): 405(M+1).

Workup

  1. concentrationConcentrate the solution to dryness
  2. custompurify the resulting orange semisolid by column chromatography (0 to 10% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-be91b72b58ff434f91082153df305014
Source dataset
uspto-grants-2015_03
Patent number
US08969555B2

Reaction notes

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