Azido(trimethyl)stannane → HCID 178451517, compound

HRID 602962Notes

Reaction equation

[C:1]([C:3]1[N:4]=[CH:5][C:6]2[CH2:11][N:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:9][C:7]=2[N:8]=1)#[N:2].[N:19]([Sn](C)(C)C)=[N+:20]=[N-:21]>C1(C)C=CC=CC=1>[NH:19]1[C:1]([C:3]2[N:4]=[CH:5][C:6]3[CH2:11][N:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:9][C:7]=3[N:8]=2)=[N:2][N:21]=[N:20]1

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of tert-butyl 2-cyano-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidine-6-carboxylate (Intermediate 9, Step D) (71 mg, 0.29 mmol) in toluene was added azidotrimethyltin (596 mg, 2.9 mmol). The resulting mixture was heated at 110° C. overnight. After the solvent was removed under reduced pressure, the residue was purified by reverse-phase silica gel chromatography (gradient 5-50% acetonitrile in water containing 0.1% TFA) to yield tert-butyl 2-(1H-tetrazol-5-yl)-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidine-6-carboxylate. The product was treated as described for Intermediate 9, Step E, to yield the title compound.

Workup

customAfter the solvent was removed under reduced pressure
customthe residue was purified by reverse-phase silica gel chromatography (gradient 5-50% acetonitrile in water containing 0.1% TFA)

Sources & evidence

ORD record: ord-a2e4521f41304a8682bb751db6663fbc
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07906649B2

Reaction notes

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