Azido(trimethyl)stannane → HCID 178448722, compound

HRID 369474Notes

Reaction equation

HRID 369474 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]2=[C:9]([S:23][CH2:24][CH2:25][CH2:26][C:27]#[N:28])[N:10]([CH2:12][C:13]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:16]=[CH:15][CH:14]=3)[CH:11]=[C:5]2[N:4]([CH2:29][CH:30]([CH3:32])[CH3:31])[C:3]1=[O:33].C[Sn]([N:38]=[N+:39]=[N-:40])(C)C>C1(C)C=CC=CC=1>[NH:38]1[C:27]([CH2:26][CH2:25][CH2:24][S:23][C:9]2[N:10]([CH2:12][C:13]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:16]=[CH:15][CH:14]=3)[CH:11]=[C:5]3[C:6]=2[C:7](=[O:8])[N:2]([CH3:1])[C:3](=[O:33])[N:4]3[CH2:29][CH:30]([CH3:31])[CH3:32])=[N:28][N:40]=[N:39]1

Participants

4

Reactant 2

HCID 5104973Azido(trimethyl)stannaneHCID 183629264-[(2,3,4,6-Tetrahydro-3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)-2,4-dioxo-1H-pyrrolo[3,4-d]pyrimidin-5-yl)thio]butanenitrile

Product 1

HCID 178448722HCID 178448722, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The compound of Example 18, 4-[(2,3,4,6-tetrahydro-3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)-2,4-dioxo-1 H-pyrrolo[3,4-d]pyrimidin-5-yl)thio]butanenitrile (98 mg) was dissolved in toluene (20 ml) and trimethyltin azide (100 mg) was added. The solution was heated under reflux for 110 hours, then the solvent was evaporated and the residue was chromatographed, eluting with ethanol:dichloromethan(1:19), to give the title compound (30 mg).

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux for 110 hours
  3. customthe solvent was evaporated
  4. customthe residue was chromatographed
  5. washeluting with ethanol:dichloromethan(1:19)

Sources & evidence

ORD record
ord-9cbba4e098894a939e198a156ed41930
Source dataset
uspto-grants-2000_10
Patent number
US06136974

Reaction notes

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