Sodium hydride → HCID 77107025, compound

HRID 2201237Notes

Reaction equation

HRID 2201237 reaction equation
[H-].[Na+].CS(O[CH2:8][C:9]([CH3:37])([CH3:36])[CH:10]([C:30]1[S:31][CH:32]=[C:33]([Cl:35])[N:34]=1)[C:11]1[NH:12][C:13]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:14]2[C:19](=[O:20])[N:18]([CH3:21])[C:17](=[O:22])[N:16]([CH3:23])[C:15]=12)(=O)=O>C1COCC1>[Cl:35][C:33]1[N:34]=[C:30]([CH:10]2[C:11]3[N:12]([C:13]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)=[C:14]4[C:19](=[O:20])[N:18]([CH3:21])[C:17](=[O:22])[N:16]([CH3:23])[C:15]4=3)[CH2:36][C:9]2([CH3:8])[CH3:37])[S:31][CH:32]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 86723472HCID 86723472, compound

Product 1

HCID 77107025HCID 77107025, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% wt., 38.0 mg, 0.950 mmol) was added to a solution of 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-dimethylpropyl methanesulfonate (170 mg, 0.317 mmol) in THF (10 mL). The mixture was stirred at room temperature for 5 mins. The reaction was quenched with water 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 20-100% EtOAc/hexane afforded the title compound.

Workup

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

Sources & evidence

ORD record
ord-97ffda4c96b44ebd9ff275fc5e7c3b9c
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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