Dibutyltin oxide → HCID 178438341, compound

HRID 354189Notes

Reaction equation

[CH2:1]([O:5][C:6]1[C:13]([C:14]2[NH:15][C:16](=[O:27])[C:17]3[C:18](=[C:20]([CH2:24][CH2:25][CH3:26])[N:21]([CH3:23])[N:22]=3)[N:19]=2)=[CH:12][C:9]([C:10]#[N:11])=[CH:8][N:7]=1)[CH:2]([CH3:4])[CH3:3].C[Si]([N:32]=[N+:33]=[N-:34])(C)C.C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1>[CH2:1]([O:5][C:6]1[C:13]([C:14]2[NH:15][C:16](=[O:27])[C:17]3[C:18](=[C:20]([CH2:24][CH2:25][CH3:26])[N:21]([CH3:23])[N:22]=3)[N:19]=2)=[CH:12][C:9]([C:10]2[NH:34][N:33]=[N:32][N:11]=2)=[CH:8][N:7]=1)[CH:2]([CH3:4])[CH3:3]

Participants

Conditions

Temperature: 80 °C

Procedure

5-[2-Isobutoxy-5-cyano-3-pyridinyl]-2-methyl-3-propyl-2,6-dihydro-7H-pyrazolo[4,3-a]pyrimidin-7-one (Example 36) (200 mg, 0.55 mmol), trimethylsilylazide (0.069 mL, 0.54 mmol) and dibutyltin oxide (54 mg, 0.22 mmol) were heated at 80° C. in toluene (10 mL) for 14 h. The reaction mixture was transferred to a PTFE lined sealed vessel, a further 0.069 mL trimethylsilylazide added and the reaction heated at 80° C. for a further 5 h. After cooling and filtering the filtrate was diluted with pentane. Further solid precipitated and this was combined with the original precipitate and purified by flash column chromatography (eluting with dichloromethane/methanol/ammonia in a ratio of 5:1:0.1) to give 144 mg product.

Workup

customlined sealed vessel
temperatureAfter cooling
filtrationfiltering the filtrate
additionwas diluted with pentane
customFurther solid precipitated
custompurified by flash column chromatography (
washeluting with dichloromethane/methanol/ammonia in a ratio of 5:1:0.1)

Sources & evidence

ORD record: ord-1e09a3e5085643fc89593b74866e3589
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06756373B1

Reaction notes

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