Allyltributylstannane → 7-(1-(4-Chlorothiazol-2-yl)but-3-en-1-yl)-5-(3-fluorophenyl)-1,3-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

HRID 2201257Notes

Reaction equation

HRID 2201257 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([CH:7](O)[C:8]2[NH:9][C:10]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=3)=[C:11]3[C:16](=[O:17])[N:15]([CH3:18])[C:14](=[O:19])[N:13]([CH3:20])[C:12]=23)[S:5][CH:6]=1.[CH2:29]([Sn](CCCC)(CCCC)CCCC)[CH:30]=[CH2:31]>C1COCC1>[Cl:1][C:2]1[N:3]=[C:4]([CH:7]([C:8]2[NH:9][C:10]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=3)=[C:11]3[C:16](=[O:17])[N:15]([CH3:18])[C:14](=[O:19])[N:13]([CH3:20])[C:12]=23)[CH2:31][CH:30]=[CH2:29])[S:5][CH:6]=1

Participants

4

Reactant 2

HCID 90628AllyltributylstannaneHCID 867234957-((4-Chlorothiazol-2-yl)(hydroxy)methyl)-5-(3-fluorophenyl)-1,3-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

Product 1

HCID 867234987-(1-(4-Chlorothiazol-2-yl)but-3-en-1-yl)-5-(3-fluorophenyl)-1,3-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Boron trifluoride THF complex (0.205 mL, 1.861 mmol) was added to a solution of 7-((4-chlorothiazol-2-yl)(hydroxy)methyl)-5-(3-fluorophenyl)-1,3-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (870 mg, 2.067 mmol) and allyltri-n-butyltin (0.641 mL, 2.067 mmol) were dissolved in THF (15 mL). The mixture was stirred at room temp. for 20 mins. The reaction mixture was quenched with saturated NaHCO3(aq) and extracted with EtOAc. The organic extracts were washed with 1M KF(aq) (1×), brine (1×), dried over sodium sulfate and evaporated under vacuum. Purification by chromatography on silica, eluting with 10-60% EtOAc/hexane, afforded the title compound.

Workup

  1. customThe reaction mixture was quenched with saturated NaHCO3(aq)
  2. extractionextracted with EtOAc
  3. washThe organic extracts were washed with 1M KF(aq) (1×), brine (1×)
  4. dry with materialdried over sodium sulfate
  5. customevaporated under vacuum
  6. customPurification by chromatography on silica
  7. washeluting with 10-60% EtOAc/hexane

Sources & evidence

ORD record
ord-76c984fc1d1d455e82b3cb85ef89692e
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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