Triethylamine → 2-((4-Chlorothiazol-2-yl)(5-(3-fluorophenyl)-1,3-dimethyl-2,4-dioxo-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-7-yl)methyl)allyl methanesulfonate

HRID 2201265Notes

Reaction equation

HRID 2201265 reaction equation
CS([O:5][S:6]([CH3:9])(=[O:8])=[O:7])(=O)=O.[Cl:10][C:11]1[N:12]=[C:13]([CH:16]([C:22]2[NH:23][C:24]([C:35]3[CH:40]=[CH:39][CH:38]=[C:37]([F:41])[CH:36]=3)=[C:25]3[C:30](=[O:31])[N:29]([CH3:32])[C:28](=[O:33])[N:27]([CH3:34])[C:26]=23)[CH:17]([CH2:20]O)[CH2:18]O)[S:14][CH:15]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:9][S:6]([O:5][CH2:20][C:17]([CH:16]([C:13]1[S:14][CH:15]=[C:11]([Cl:10])[N:12]=1)[C:22]1[NH:23][C:24]([C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([F:41])[CH:36]=2)=[C:25]2[C:30](=[O:31])[N:29]([CH3:32])[C:28](=[O:33])[N:27]([CH3:34])[C:26]=12)=[CH2:18])(=[O:7])=[O:8]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 81560Methanesulfonic anhydride2×HCID 86723504HCID 86723504, compound

Product 1

HCID 867235062-((4-Chlorothiazol-2-yl)(5-(3-fluorophenyl)-1,3-dimethyl-2,4-dioxo-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-7-yl)methyl)allyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonic anhydride (1699 mg, 9.75 mmol) was added to a solution of 7-(1-(4-chlorothiazol-2-yl)-3-hydroxy-2-(hydroxymethyl)propyl)-5-(3-fluorophenyl)-1,3-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (934 mg, 1.950 mmol) and triethylamine (1.631 mL, 11.70 mmol) in DCM (20 mL). The mixture was stirred at room temperature for 16 hours. Further portions of triethylamine (1.631 mL, 11.70 mmol) and methanesulfonic anhydride (1699 mg, 9.75 mmol) were added as necessary to allow the reaction to run to completion. The reaction was quenched with saturated NaHCO3(aq) and extracted with DCM (3×). The combined organic extracts were passed through a hydrophobic frit and evaporated under vacuum. Purification by chromatography on silica, eluting with 20-100% EtOAc/hexane, afforded the title compound.

Workup

  1. customthe reaction
  2. customThe reaction was quenched with saturated NaHCO3(aq)
  3. extractionextracted with DCM (3×)
  4. customevaporated under vacuum
  5. customPurification by chromatography on silica
  6. washeluting with 20-100% EtOAc/hexane

Sources & evidence

ORD record
ord-779f3b0f4af64824a54cd78e1818c8c3
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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