Sodium hydride → HCID 77107829, compound

HRID 2201266Notes

Reaction equation

HRID 2201266 reaction equation
[H-].[Na+].CS(O[CH2:8][C:9]([CH:11]([C:32]1[S:33][CH:34]=[C:35]([Cl:37])[N:36]=1)[C:12]1[NH:13][C:14]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=2)=[C:15]2[C:20](=[O:21])[N:19]([CH3:22])[C:18](=[O:23])[N:17]([CH3:24])[C:16]=12)=[CH2:10])(=O)=O>C1COCC1>[Cl:37][C:35]1[N:36]=[C:32]([CH:11]2[C:12]3[N:13]([C:14]([C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=4)=[C:15]4[C:20](=[O:21])[N:19]([CH3:22])[C:18](=[O:23])[N:17]([CH3:24])[C:16]4=3)[CH2:10][C:9]2=[CH2:8])[S:33][CH:34]=1

Participants

4

Reactant 2

HCID 24758Sodium hydride2×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

Product 1

HCID 77107829HCID 77107829, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% wt. in mineral oil, 31.2 mg, 0.779 mmol) was added to a solution of 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 (140 mg, 0.260 mmol) in THF (8 mL). The mixture was stirred at room temperature for 2 hours. A further portion of sodium hydride (31.2 mg, 0.779 mmol) was added to allow the reaction to run to completion. The reaction was quenched with water 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 water
  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-f6e40be167e646698032dfeb8f139ad6
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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