Azidotrimethylsilane → HCID 178525384, compound

HRID 870594Notes

Reaction equation

HRID 870594 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[CH2:33][N:32]([C:34]([O:36][CH2:37][CH2:38][CH2:39][C:40]#[CH:41])=[O:35])[CH2:31][CH2:30][C:28]=2[N:29]=1.[N:42]([Si](C)(C)C)=[N+:43]=[N-:44]>CN(C)C=O.O.C(OCC)(=O)C.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[CH2:33][N:32]([C:34]([O:36][CH2:37][CH2:38][CH2:39][C:40]3[N:42]=[N:43][NH:44][CH:41]=3)=[O:35])[CH2:31][CH2:30][C:28]=2[N:29]=1

Participants

8

Reactant 3

HCID 78378AzidotrimethylsilaneHCID 66586226sodium L-ascorbic acidHCID 86726557HCID 86726557, compound

Product 1

HCID 178525384HCID 178525384, compoundYield 35%

Reagents, catalysts & solvents 4

HCID 24463Copper sulfate pentahydrateCatalystHCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add copper(II)sulfate pentahydrate (0.090 g; 0.2 equiv; 0.36 mmoles) and L-ascorbic acid sodium salt (0.714 g; 2.0 equiv; 3.61 mmoles) to a deoxygenated solution of pent-4-yn-1-yl 2-(2,3-dihydro-1H-inden-2-ylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (0.754 g; 1.0 equiv; 1.80 mmoles) in dimethylformamide (15 mL) and water (15 mL). Add azidotrimethylsilane (1.92 mL; 8 equiv; 14.42 mmoles) and heat the reaction to 90° C. for 3 hours. Dilute the reaction mixture with water (250 mL) and ethyl acetate. Extract the mixture with ethyl acetate (3×50 mL). Wash the combined organic extracts with water (3×) and brine, dry over sodium sulfate, filter, and concentrate to a tan/orange oil. Purify the crude product by column chromatography (0 to 5% methanol in dichloromethane) to afford 3-(1H-1,2,3-triazol-4-yl)propyl 2-(2,3-dihydro-1H-inden-2-ylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (0.26 g; 35%): MS (m/z): 420(M+1).

Workup

  1. customthe reaction to 90° C. for 3 hours
  2. extractionExtract the mixture with ethyl acetate (3×50 mL)
  3. washWash the combined organic extracts with water (3×) and brine
  4. dry with materialdry over sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate to a tan/orange oil
  7. customPurify the crude product by column chromatography (0 to 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-5825e55271bf4c61894a9066b7c6f74b
Source dataset
uspto-grants-2015_03
Patent number
US08969555B2

Reaction notes

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