Azido(trimethyl)stannane → HCID 178461871, compound

HRID 2300882Notes

Reaction equation

HRID 2300882 reaction equation
[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][C:23]([C:25]#[N:26])=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Sn]([N:31]=[N+:32]=[N-:33])(C)C>C1(C)C(C)=CC=CC=1>[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][C:23]([C:25]5[NH:33][N:32]=[N:31][N:26]=5)=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 5104973Azido(trimethyl)stannaneHCID 59924666HCID 59924666, compound

Product 1

HCID 178461871HCID 178461871, compoundYield 26.6%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

2-[(S)-1-Phenylethylamino]-4-[5-cyanobenzimidazol-1-yl ]pyrimidine (20 mg) and trimethylstannylazide (18 mg) were heated (110° C.) in xylene for 15 hours. Upon cooling, the solution was evaporated to dryness and the residue was purified with preparatory thin-layer chromatography (SiO2, 5% MeOH/1% triethylamine in CH2Cl2) to yield 6 mg of the title compound Mass spectrum (ESI) 384.1 (M+1).

Workup

  1. temperatureUpon cooling
  2. customthe solution was evaporated to dryness
  3. customthe residue was purified with preparatory thin-layer chromatography (SiO2, 5% MeOH/1% triethylamine in CH2Cl2)

Sources & evidence

ORD record
ord-12e9cadfe57c47a49b95d9f9c7f1df94
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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