Tetrahydrofuran → HCID 118598658, compound

HRID 1050368Notes

Reaction equation

HRID 1050368 reaction equation
[H-].[Na+].[I-].C[S+](C)C.[CH3:8][O:9][C:10]1[CH:50]=[CH:49][C:13]([CH2:14][N:15]2[C:42](=[O:43])[C:18]3=[C:19]([CH:40]=[O:41])[CH:20]=[C:21]([N:24]([CH2:31][C:32]4[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=4)[C:25]4[CH:30]=[CH:29][N:28]=[CH:27][N:26]=4)[C:22](=[O:23])[N:17]3[C:16]32[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]3)=[CH:12][CH:11]=1.O1CCC[CH2:52]1>CS(C)=O.O>[CH3:8][O:9][C:10]1[CH:50]=[CH:49][C:13]([CH2:14][N:15]2[C:42](=[O:43])[C:18]3=[C:19]([CH:40]4[CH2:52][O:41]4)[CH:20]=[C:21]([N:24]([CH2:31][C:32]4[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=4)[C:25]4[CH:30]=[CH:29][N:28]=[CH:27][N:26]=4)[C:22](=[O:23])[N:17]3[C:16]32[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]3)=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 75127Trimethylsulfonium iodideHCID 118598813HCID 118598813, compound

Product 1

HCID 118598658HCID 118598658, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

A suspension of sodium hydride (50% dispersion washed free of mineral oil, 90 mg, 1.87 mmol) in dimethylsulfoxide (2 mL) is heated to 65° C. under argon for 1 h. The oil bath is removed and to the clear solution is added tetrahydrofuran (2 mL). The solution is cooled to −15° C. and treated with a solution of trimethylsulfonium iodide (0.35 g, 1.72 mmol) in dimethylsulfoxide (2 mL). After 3 min a solution of 2′-(4-methoxybenzyl)-6′-((4-methoxybenzyl)(pyrimidin-4-yl)amino)-1′,5′-dioxo-1′,5′-dihydro-2′H-spiro[cyclohexane-1,3′-imidazo[1,5-a]pyridine]-8′-carbaldehyde (4, 1 g, 1.72 mmol) in 3 ml. of tetrahydrofuran is added. The reaction is stirred overnight. The resulting mixture is poured into water and extracted with ethyl acetate. The extracts are washed with water, dried and evaporated to afford 2′-(4-methoxybenzyl)-6′-((4-methoxybenzyl)(pyrimidin-4-yl)amino)-8′-(oxiran-2-yl)-2′H-spiro[cyclohexane-1,3′-imidazo[1,5-a]pyridine]-1′,5′-dione (5).

Workup

  1. customThe oil bath is removed and to the clear solution
  2. additionis added tetrahydrofuran (2 mL)
  3. temperatureThe solution is cooled to −15° C.
  4. extractionextracted with ethyl acetate
  5. washThe extracts are washed with water
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-1101c5c152644e56a31c20c2479bb7e2
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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