Silane, ((1-methoxy-2-methyl-1-propenyl)oxy)trimethyl- → Methyl 3-(4-chlorothiazol-2-yl)-3-(1,3-dimethyl-2,4-dioxo-5-phenyl-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-7-yl)-2,2-dimethylpropanoate

HRID 2201235Notes

Reaction equation

HRID 2201235 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]=[CH:23][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.[CH3:28][O:29][C:30]([O:34][Si](C)(C)C)=[C:31]([CH3:33])[CH3:32]>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]=[CH:23][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)[C:31]([CH3:33])([CH3:32])[C:30]([O:29][CH3:28])=[O:34])[S:5][CH:6]=1

Participants

4

Reactant 2

HCID 552336Silane, ((1-methoxy-2-methyl-1-propenyl)oxy)trimethyl-HCID 867234707-((4-chlorothiazol-2-yl)(hydroxy)methyl)-1,3-dimethyl-5-phenyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

Product 1

HCID 86723469Methyl 3-(4-chlorothiazol-2-yl)-3-(1,3-dimethyl-2,4-dioxo-5-phenyl-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-7-yl)-2,2-dimethylpropanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Boron trifluoride THF complex (0.028 mL, 0.255 mmol) was added to a solution of 7-((4-chlorothiazol-2-yl) (hydroxy)methyl)-1,3-dimethyl-5-phenyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (114 mg, 0.283 mmol) and commercially available ((1-methoxy-2-methylprop-1-en-1-yl)oxy)trimethylsilane (0.143 mL, 0.707 mmol) in THF (5 mL). The mixture was stirred at room temperature for 5 minutes. The reaction was quenched with saturated NaHCO3(aq) and extracted with DCM (2×). The combined organic extracts were passed through a hydrophobic frit and evaporated under vacuum. Purification by chromatography on silica, eluting with 20-80% EtOAc/hexane afforded the title compound.

Workup

  1. customThe reaction was quenched with saturated NaHCO3(aq)
  2. extractionextracted with DCM (2×)
  3. customevaporated under vacuum
  4. customPurification by chromatography on silica
  5. washeluting with 20-80% EtOAc/hexane

Sources & evidence

ORD record
ord-ef9decb81e9d4cabaf7918ddd70fbadb
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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