Tributyltin azide → HCID 178462870, compound

HRID 1893915Notes

Reaction equation

HRID 1893915 reaction equation
C([Sn]([N:14]=[N+:15]=[N-:16])(CCCC)CCCC)CCC.[NH2:17][C:18]1[N:19]=[C:20]([CH3:33])[C:21]2[CH:27]=[C:26]([C:28]#[N:29])[C:25](=[O:30])[N:24]([CH2:31][CH3:32])[C:22]=2[N:23]=1>C1(C)C=CC=CC=1>[NH2:17][C:18]1[N:19]=[C:20]([CH3:33])[C:21]2[CH:27]=[C:26]([C:28]3[NH:16][N:15]=[N:14][N:29]=3)[C:25](=[O:30])[N:24]([CH2:31][CH3:32])[C:22]=2[N:23]=1

Participants

4

Reactant 2

HCID 4984872Tributyltin azideHCID 57606980HCID 57606980, compound

Product 1

HCID 178462870HCID 178462870, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
140 °C

Procedure

Tributyltin azide (660 μL, 2.41 mmol) was added to a flask charged with 2-amino-8-ethyl-4-methyl-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidine-6-carbonitrile (0.184 g, 0.803 mmol) in anhydrous toluene (5.0 mL). The reaction was fitted with a reflux condenser and heated to 140° C. under a nitrogen atmosphere. After 20 h, the reaction was cooled to room temperature and the precipitate collected by vacuum filtration and washed with absolute ethanol to give 2-amino-8-ethyl-4-methyl-6-(1H-tetrazol-5-yl)pyrido[2,3-d]pyrimidin-7(8H)-one (98 mg, 45% yield) as a light brown solid: 1H NMR (400 MHz, 20% DCl in D2O): δ 6.97 (s, 1H), 2.42 (q, J=7.2 Hz, 2H), 0.953 (s, 3H), −0.73 (t, J=7.2 Hz, 3H); MS (EI) for C11H11N8O: 271.0 (MH+).

Workup

  1. customThe reaction was fitted with a reflux condenser
  2. temperaturethe reaction was cooled to room temperature
  3. filtrationthe precipitate collected by vacuum filtration
  4. washwashed with absolute ethanol

Sources & evidence

ORD record
ord-03d5fd25a242449ba9e266d97e87cdaf
Source dataset
uspto-grants-2013_08
Patent number
US08513266B2

Reaction notes

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